Methanol → HCID 49838811, compound

HRID 2391091Notes

Reaction equation

HRID 2391091 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH:27][C:28]([O:30][CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][Si](C(C)(C)C)(C)C)[CH:34]=4)[CH3:32])=[O:29])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.CO.[OH-].[Li+]>O>[OH:39][C:35]1[CH:34]=[C:33]([CH:31]([O:30][C:28]([NH:27][C:22]2[C:23]([CH3:26])=[N:24][O:25][C:21]=2[C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:6]4([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]4)=[CH:14][CH:13]=3)=[CH:16][CH:17]=2)=[O:29])[CH3:32])[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66660665HCID 66660665, compound

Product 1

HCID 49838811HCID 49838811, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1-[4′-(4-{1-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-ethoxycarbonylamino}-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.400 g, 0.63 mmol) in 3:1 MeOH:H2O (10 mL) was treated with excess lithium hydroxide. The reaction was stirred overnight at 60° C., and then acidified and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-aa35d170b7664518ba1d0f12fd92c1fd
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

Loading…