Potassium Hydroxide → HCID 86584794, compound

HRID 1356215Notes

Reaction equation

HRID 1356215 reaction equation
C([O:3][C:4](=[O:51])[CH:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:29][S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:16](=[O:28])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:10][C:9]=1[N:39]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH3:40])[F:6])C.[OH-].[K+]>CCO>[C:33]1([S:30]([NH:29][C@H:15]([C:16](=[O:28])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:14][C:11]2[CH:12]=[CH:13][C:8]([O:7][CH:5]([F:6])[C:4]([OH:51])=[O:3])=[C:9]([N:39]([C:41]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:42])[CH3:40])[CH:10]=2)(=[O:32])=[O:31])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86584793HCID 86584793, compound

Product 1

HCID 86584794HCID 86584794, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[4-[(2S)-2-Benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-(benzyloxycarbonyl-methyl-amino)-phenoxy]-fluoro-acetic acid ethyl ester of Step C is dissolved in EtOH (2 mL) and 1N KOH (0.32 mL) is added. The mixture is stirred overnight. The solution is concentrated, and suspended in ETOAC and loaded on silica gel plug. The plug is washed with ETOAC (100 mL) to remove the impurities. The product is eluted from the plug by using 2% HOAC in ETOAC. The filtrate is concentrated to provide [4-[(2S)-2-benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-(benzyloxycarbonyl-methyl-amino)-phenoxy]-fluoro-acetic acid.

Workup

  1. concentrationThe solution is concentrated
  2. washThe plug is washed with ETOAC (100 mL)
  3. customto remove the impurities
  4. washThe product is eluted from the plug
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-1e90fef6d4bb4164afb08ec8e125f890
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

Loading…