Reacción #1702087

ord-3502db47a3504516bbce2a444619bc4c

Ecuación de reacción

CC(C)(C)C#Cc1cc(N(CCO[Si](C)(C)C(C)(C)C)C(=O)[C@H]2CC[C@H](C)CC2)c(C(=O)O)s1
3-[[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid
CCN(CC)CC.F.F.F
triethylaminetrihydrofluoride
→
CC(C)(C)C#Cc1cc(N(CCO)C(=O)[C@H]2CC[C@H](C)CC2)c(C(=O)O)s1
5-(3,3-Dimethyl-but-1-ynyl)-3-[(2-hydroxy-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid
Rendimiento 39.3%

Reactantes

CC(C)(C)C#Cc1cc(N(CCO[Si](C)(C)C(C)(C)C)C(=O)[C@H]2CC[C@H](C)CC2)c(C(=O)O)s1
3-[[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid
CCN(CC)CC.F.F.F
triethylaminetrihydrofluoride

Reactivos

Ninguno

Disolventes

C1CCOC1
THF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrovolatiles were removed under vacuum
  2. 2
    Otrothe residue was purified by silica gel chromatography (0-10% Methanol:DCM)

Procedimiento

3-[[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid (273 mg) in THF (4 mL) was treated with triethylaminetrihydrofluoride (0.5 mL). After 1 hour, volatiles were removed under vacuum and the residue was purified by silica gel chromatography (0-10% Methanol:DCM) to provide 83 mg of 5-(3,3-Dimethyl-but-1-ynyl)-3-[(2-hydroxy-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08765722B2uspto-grants-2014_07