Potassium Carbonate → HCID 86584793, compound

HRID 1356214Notes

Reaction equation

HRID 1356214 reaction equation
[CH2:1]([O:8][C:9](=[O:44])[N:10]([C:12]1[CH:17]=[C:16]([CH2:18][C@H:19]([NH:33][S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:20](=[O:32])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:15]=[CH:14][C:13]=1[OH:43])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:51]([O:53][C:54](=[O:58])[CH:55](Br)[F:56])[CH3:52]>CN(C=O)C>[CH2:51]([O:53][C:54](=[O:58])[CH:55]([O:43][C:13]1[CH:14]=[CH:15][C:16]([CH2:18][C@H:19]([NH:33][S:34]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)(=[O:36])=[O:35])[C:20](=[O:32])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:17][C:12]=1[N:10]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:44])[CH3:11])[F:56])[CH3:52]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl ester2×HCID 69129541HCID 69129541, compound

Product 1

HCID 86584793HCID 86584793, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{5-[(2S)-2-Benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-hydroxy-phenyl}-methyl-carbamic acid benzyl ester of Step B (100 mg, 0.16 mmol) is dissolved in DMF (2 mL). Potassium carbonate (23 mg, 0.16 mmol) and bromo-fluoro-acetic acid ethyl ester (20 μl, 0.16 mmol) are added. The mixture is stirred at RT overnight. 40 μl (0.32 mmol) more of bromo-fluoro-acetic acid ethyl ester is added and stirred overnight. The mixture is purified through a silica plug to provide [4-[(2S)-2-benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-(benzyloxycarbonyl-methyl-amino)-phenoxy]-fluoro-acetic acid ethyl ester which is used without further purification.

Workup

  1. stirringstirred overnight
  2. customThe mixture is purified through a silica plug

Sources & evidence

ORD record
ord-c80a505d10bc487c91bbc2f67fa52d46
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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