ChemicalBook > CAS DataBase List > (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Product Name
(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS No.
101410-18-8
Chemical Name
(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
Synonyms
1-Pyrrolidineca;BOC-(S)-Pyrrolidine-2-Thiocarboxamide;(S)-1-Boc-pyrrolidine-2-carbothioamide;N-BOC-(S)-Pyrrolidine-2-thiocarboxamide;TERT-BUTYL2(S)-THIOCARBAMOYLPYRROLIDINE-1-CARBOXYLATE;tert-butyl (S)-2-carbamothioylpyrrolidine-1-carboxylate;(S)-tert-butyl 2-thiocarbaMoylpyrrolidine-1-carboxylate;tert-butyl (2S)-2-carbamothioylpyrrolidine-1-carboxylate;2-Methyl-2-propanyl (2S)-2-carbamoyl-1-pyrrolidinecarboxylate;2R-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
CBNumber
CB5386725
Molecular Formula
C10H18N2O2S
Formula Weight
230.33
MOL File
101410-18-8.mol
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(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Property

Melting point:
195-199 °C(Solv: tetrahydrofuran (109-99-9))
Boiling point:
339.5±52.0 °C(Predicted)
Density 
1.191±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
pka
12.98±0.20(Predicted)
Appearance
White to off-white Solid
InChI
InChI=1S/C10H18N2O2S/c1-10(2,3)14-9(13)12-6-4-5-7(12)8(11)15/h7H,4-6H2,1-3H3,(H2,11,15)/t7-/m0/s1
InChIKey
KPAOKCBKJXBXNI-ZETCQYMHSA-N
SMILES
N1(C(OC(C)(C)C)=O)CCC[C@H]1C(N)=S
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

TRC
Product number
B810415
Product name
(S)-tert-Butyl2-Carbamothioylpyrrolidine-1-carboxylate
Packaging
50mg
Price
$130
Updated
2021/12/16
AK Scientific
Product number
B399
Product name
(S)-2-Thiocarbamoyl-pyrrolidine-1-carboxylicacidtert-butylester
Packaging
250mg
Price
$139
Updated
2021/12/16
ChemScene
Product number
CS-0047030
Product name
tert-Butyl(S)-2-carbamothioylpyrrolidine-1-carboxylate
Purity
97.26%
Packaging
1g
Price
$85
Updated
2021/12/16
Activate Scientific
Product number
AS36058
Product name
(S)-(1-Boc)-2-carbamothioylpyrrolidine
Purity
95+% ee
Packaging
1g
Price
$265
Updated
2021/12/16
ChemScene
Product number
CS-0047030
Product name
tert-Butyl(S)-2-carbamothioylpyrrolidine-1-carboxylate
Purity
97.26%
Packaging
5g
Price
$270
Updated
2021/12/16
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(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties,Usage,Production

Synthesis

35150-07-3

117175-41-4

General procedure for the synthesis of tert-butyl (R)-2-thiocarboxamido pyrrolidine-1-carboxylate from N-tert-butoxycarbonyl-L-prolinamide: (S)-1-(tert-butoxycarbonyl)prolinamide (9.0 g, 42.0 mmol) and Lawesson's reagent (8.5 g, 21.0 mmol) were dissolved in anhydrous THF (55 mL) and the reaction was stirred for 3.5 hours at room temperature under nitrogen protection. The reaction was stirred at room temperature for 3.5 h under nitrogen protection. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Saturated aqueous NaHCO3 (100 mL) was added to the residue and stirring was continued for 1 hour. The aqueous phase suspension was extracted with EtOAc/CH2Cl2 (1:1, 400 mL), the organic phase was washed with saturated aqueous NaHCO3 solution (2 x 100 mL), and the combined aqueous phases were then extracted with EtOAc/CH2Cl2 (200 mL). All organic extracts were combined, dried with Na2SO4 and concentrated under reduced pressure to give tert-butyl (S)-2-thiocarbonylpyrrolidine-1-carboxylate as a white solid (8.74 g, 90% yield) with a melting point (EtOAc) of 190-192 °C. [α]D -103.4 (c 1.00, CHCl3). IR (KBr) 3380, 3202, 2981, 2881, 1671, 1411, 1166 cm-1. 1H NMR (400 MHz, CDCl3) δ= 1.41-1.50 (m, 9H), 1.65-2.75 (m, 4H), 3.22- 3.74 (m, 2H), 4.67 (dd, J = 8.0 and 3.6 Hz, 1H) ppm. HRMS (ESI) m/z calculated value C10H19N2O2S (M + H) 231.1162, measured value 231.1161.

References

[1] Journal of the American Chemical Society, 2002, vol. 124, # 6, p. 916 - 917
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2229 - 2233
[3] Tetrahedron Letters, 2011, vol. 52, # 42, p. 5435 - 5437
[4] Patent: US2011/65726, 2011, A1. Location in patent: Page/Page column 12
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 228 - 247

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Raw materials

Preparation Products

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View Lastest Price from (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER manufacturers

Career Henan Chemical Co
Product
(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 101410-18-8
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200kg
Release date
2020-01-08

101410-18-8, (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTERRelated Search:

(S)-1-N-Boc-2-methylpiperazine D-1-N-Boc-prolinamide L-Prolinamide TERT-BUTYL 2-AMINO-2-THIOXOETHYLCARBAMATE 2-AMINO-THIOPROPIONAMIDE (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (R)-2-(Aminomethyl)-1-N-Boc-pyyrolidine (1-BOC-PYRROLIDINE)-2-CARBOTHIOAMIDE BOC-L-ALANINE THIOAMIDE (S)-1-N-Boc-2-(aminomethyl)pyrrolidine N-Boc-cis-4-Hydroxy-L-proline methyl ester (S)-Methyl-2-Boc-AMino-4-pentenoic acid (2R,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid N-BOC-SERINOL, 97 N-Boc-trans-4-amino-L-proline methyl ester hydrochloride N-Boc-Trans-4-Hydroxy-D-proline methyl ester N-BOC-CYCLOHEXAMIDE N-Boc-N-methyl-(S)-2-allylglycine

  • 2R-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
  • (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
  • TERT-BUTYL2(S)-THIOCARBAMOYLPYRROLIDINE-1-CARBOXYLATE
  • 1-Pyrrolidinecarboxylic acid, 2-(aMinothioxoMethyl)-, 1,1-diMethylethyl ester, (2S)-
  • 1-Pyrrolidineca
  • (S)-tert-butyl 2-thiocarbaMoylpyrrolidine-1-carboxylate
  • (S)-2-Thiocarbamoylpyrrolidine-1-carboxylic acid tert-butyl este
  • tert-butyl (S)-2-carbamothioylpyrrolidine-1-carboxylate
  • (S)-tert-butyl2-carbamothioylpyrrolidine-1-carboxylate(WX191807)
  • tert-butyl (2S)-2-carbamothioylpyrrolidine-1-carboxylate
  • (S)-1-Boc-pyrrolidine-2-carbothioamide
  • 2-Methyl-2-propanyl (2S)-2-carbamoyl-1-pyrrolidinecarboxylate
  • N-BOC-(S)-Pyrrolidine-2-thiocarboxamide
  • (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL...
  • BOC-(S)-Pyrrolidine-2-Thiocarboxamide
  • 101410-18-8
  • 101410-18-0