CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester Chemical Properties

Melting point:

117 - 119°C

Boiling point:

489.1±45.0 °C(Predicted)

Density 

1.28

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

11.41±0.60(Predicted)

color 

White to Off-White

InChI

InChI=1S/C16H21NO5/c1-16(2)21-13-11(8-12(18)14(13)22-16)17-15(19)20-9-10-6-4-3-5-7-10/h3-7,11-14,18H,8-9H2,1-2H3,(H,17,19)/t11-,12+,13+,14-/m1/s1

InChIKey

VPICQZQITAJOQA-ZOBORPQBSA-N

SMILES

C(OCC1=CC=CC=C1)(=O)N[C@H]1[C@@]2([H])[C@@]([H])([C@@H](O)C1)OC(C)(C)O2

CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester Usage And Synthesis

Uses

Phenylmethyl ester N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]-Carbamic acid is a useful chiral building block. It has been used in the synthesis of all-cis carbocyclic precursor of ticagrelor via oxidation/stereoselective reduction sequences.

Synthesis

Step 7: To a tetrahydrofuran:water mixture of (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopentadieno[d][1,3]dioxol-4-ol (17.0 g, 98.15 mmol, 1.00 eq.) and sodium carbonate (20.8 g, 196.24 mmol, 2.00 eq.) at 0°C (5:1, 600 mL) mixed solution, benzyl chloroformate (18.4 g, 107.86 mmol, 1.05 eq.) was slowly added. After completion of the reaction, extraction was carried out with ethyl acetate (3×200 mL) and the organic phases were combined to give the title compound N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopentaeno-1,3-dioxolan-4-yl]carbamic acid benzyl ester as a white solid (20.5 g, 68% yield) after standard post-processing. The product was characterized by 1H NMR (300 MHz, CDCl3), δ: 7.30-7.39 (m, 5H), 5.20 (s, 2H), 4.60 (d, J=5.4 Hz, 1H), 4.50 (d, J=5.4 Hz, 1H), 4.27 (s, 1H), 4.19 (d, J=5.7 Hz, 1H), 2.26 (m. 1H), 1.71 (d, J=14.4Hz, 1H), 1.47 (s, 3H), 1.28 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 6013 - 6018
[2] Patent: WO2011/17108, 2011, A2. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3598 - 3602
[4] Patent: WO2012/138981, 2012, A2. Location in patent: Page/Page column 38
[5] Patent: CN106279095, 2017, A. Location in patent: Paragraph 0023; 0046

CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester(274693-53-7)Related Product Information

• N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester
• Acetic acid, [[(3aR,4S,6R,6aS)-tetrahydro-2,2-diMethyl-6-[[(phenylMethoxy)carbonyl]aMino]-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-, ethyl ester
• Ticagrelor Related Compound 151
• Ticagrelor Related Compound 150
• TICAGRELOR
• 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid
• 4,6-dichloro-2-propylthiopyrimidine-5-amine
• 4,6-DICHLORO-5-NITRO-2-PROPYLTHIOPYRIMIDINE
• (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol
• (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate
• 1-Acetyladamantane Intermediate
• (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine. HCl
• Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[[5-aMino-6-chloro-2-(propylthio)-4-pyriMidinyl]aMino]tetrahydro-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-
• ethyCyclopropanamine, 2-(3,4-difluorophenyl)-, (1R,2S)- (REACH)
• (1R,2R)-2-(3,4-difluorophenyl)cyclopropane carboxaMide
• (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine
• Cyclopropanamine,2-(3,4-difluorophenyl)-(1R,2S) -(2R,3R)-2,3-dihydroxybutanedioate (1:1)