tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

Product Name: tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
CAS No.: 112741-49-8
Chemical Name: tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
Synonyms: tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate;CIVENTICHEM CV-2654;CIVENTICHEM CV-2653;2-Oxo-7a-hydroxy Clopidogrel;(5S,6R)-N-BoC-5,6-diphenyl-2-morpholinone;(5S,6R)-N-Boc-5,6-diphenylmorpholin-2-one;(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylMorpholine;tert-butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morph;(5R,6S)-(-)-4-Boc-5,6-diphenyl-2-Morpholinone, 98%;(2R,3S)-(-)-2,3-Diphenyl-6-oxomorpholine, N-BOC protected
CBNumber: CB2424796
Molecular Formula: C21H23NO4
Formula Weight: 353.41
MOL File: 112741-49-8.mol

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tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate Property

Melting point:: 206 °C (dec.)(lit.)
Boiling point:: 509.6±50.0 °C(Predicted)
alpha: -87 º (c=5.5 in methylene chloride)
Density: 1.175±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: Acetone (Slightly, Heated, Sonicated), Chloroform (Slightly), DMSO (Slightly, Sonicated)
form: Solid
pka: -3.28±0.60(Predicted)
color: White to Off-White
optical activity: [α]25/D 87°, c = 5.5 in methylene chloride
InChI: InChI=1S/C21H23NO4/c1-21(2,3)26-20(24)22-14-17(23)25-19(16-12-8-5-9-13-16)18(22)15-10-6-4-7-11-15/h4-13,18-19H,14H2,1-3H3/t18-,19+/m0/s1
InChIKey: MRUKRSQUUNYOFK-RBUKOAKNSA-N
SMILES: N1(C(OC(C)(C)C)=O)CC(=O)O[C@H](C2=CC=CC=C2)[C@@H]1C1=CC=CC=C1

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-37/39
WGK Germany: 3
HS Code: 2934999090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 331848
Product name: (2R,3S)-(?)-N-Boc-6-oxo-2,3-diphenylmorpholine
Purity: 98%
Packaging: 1g
Price: $52
Updated: 2023/01/07

Sigma-Aldrich

Product number: 331848
Product name: (2R,3S)-(?)-N-Boc-6-oxo-2,3-diphenylmorpholine
Purity: 98%
Packaging: 5g
Price: $197
Updated: 2023/01/07

Strem Chemicals

Product number: 08-1262
Product name: (2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic acid t-butyl ester, 98% (99% ee)
Packaging: 1g
Price: $165
Updated: 2024/03/01

TRC

Product number: O869970
Product name: (2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylicAcidtert-ButylEster
Packaging: 1g
Price: $105
Updated: 2021/12/16

Matrix Scientific

Product number: 127692
Product name: (2R,3S)-(-)-2,3-Diphenyl-6-oxomorpholine
Purity: N-BOCprotected>95%
Packaging: 1g
Price: $149
Updated: 2021/12/16

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tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate Chemical Properties,Usage,Production

Chemical Properties

tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is Off-white Solid

Uses

Tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and colla gen cross-link pyridinolines.

Uses

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and collagen cross-link pyridinolines.

Synthesis

112741-70-5

112741-49-8

N-Boc-substituted diphenylamino alcohol (1.9 g, 4.2 mmol) was dissolved in toluene (25 mL), p-TsOH (p-TsOH, 70 mg, 0.42 mmol) was added, and the reaction was heated and refluxed at 120 °C overnight. Upon completion of the reaction, it was cooled to room temperature and a solid was precipitated. The solid was collected by filtration, washed with saturated aqueous sodium chloride solution, the organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The yellow solid obtained was recrystallized by anhydrous ethanol (20 mL) to give a white solid. After filtration and drying by rotary evaporation, 1.22 g (2R,3S)-N-tert-butoxycarbonyl-2,3-diphenylmorpholin-6-one was obtained as a white solid in 85% yield.

References

[1] Patent: CN104945345, 2017, B. Location in patent: Paragraph 0105; 0107; 0116; 0118
[2] Journal of the American Chemical Society, 1988, vol. 110, # 5, p. 1547 - 1557
[3] Synlett, 2005, # 4, p. 693 - 696
[4] Organic Syntheses, 2003, vol. 80, p. 18 - 30

tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate Preparation Products And Raw materials

Raw materials

Preparation Products

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tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate Suppliers

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112741-49-8, tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylateRelated Search:

Carbamic acid, [(3S,4R)-tetrahydro-4-hydroxy-3-furanyl]-, 1,1-dimethylethyl 2-Methylmorpholine Ephedrine Phenylpropanolamine Ephedrine hemihydrate (5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one (-)-N-METHYLEPHEDRINE (R)-2-Methyl-morpholine (5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one L-(-)-Ephedrine tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate 2-(1-phenylethylamino)ethanol 1-N-BOC-2-METHYL MORPHOLINE BOC-L-Phenylglycinol (1R,2S)-2-Amino-1,2-diphenylethanol (S)-3-phenylmorpholine 5-Phenyl-2-morpholinone TERT-BUTYL (2S,3R)-(+)-6-OXO-2,3-DIPHENYL-4-MORPHOLINECARBOXYLATE

CIVENTICHEM CV-2653

CIVENTICHEM CV-2654

TERT-BUTYL (2R,3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINECARBOXYLATE

N-TERT-BUTOXYCARBONYL-(2R,3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINE

N-BOC(2R, 3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINE CARBOXYLATE

tert-butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morph

TERT-BUTYL (2R,3S)-(-)-6-OXO-2,3-DIPHENY L-4-MORPHOLINECARBOXYLATE, 99% (99% EE)

(2R,3S)-6-Oxo-2,3-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

(2R,3S)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate

(5S,6R)-N-BoC-5,6-diphenyl-2-morpholinone

(2R,3S)-tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid 1,1-Dimethylethyl Ester

4-Morpholinecarboxylicacid, 6-oxo-2,3-diphenyl-, 1,1-dimethylethyl ester, (2R,3S)-

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester,99%e.e.

(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylMorpholine

(5R,6S)-(-)-4-Boc-5,6-diphenyl-2-Morpholinone, 98%

(2R,3S)-(-)-2,3-Diphenyl-6-oxomorpholine, N-BOC protected

tert-Butyl (2R,3S)-(-)-2,3-diphenyl-6-oxomorpholine-4-carboxylate

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester

(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylMorpholine

2-Oxo-7a-hydroxy Clopidogrel

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic acid t-butyl ester, 98% (99% ee)

tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarbox

tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

ert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylic acid

(5S,6R)-N-Boc-5,6-diphenylmorpholin-2-one

(2R,3S)-tert-Butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate - [B89056]

112741-49-8

Asymmetric Synthesis

Chiral Building Blocks

Heterocyclic Building Blocks

Morpholines

API intermediates

Chiral Building Blocks

Heterocyclic Building Blocks

Morpholines