Chloroform → HCID 90370288, compound

HRID 2176045Notes

Reaction equation

HRID 2176045 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][C:12]([N:14]([CH2:18][C:19]1[CH:20]=[C:21]([CH:54]=[CH:55][CH:56]=1)[C:22]([NH:24][C:25]1[S:26][C:27]2[CH2:53][CH2:52][CH2:51][CH2:50][C:28]=2[C:29]=1[C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]2[CH:49]=[CH:48][C:44]([C:45]([OH:47])=[O:46])=[CH:43][CH:42]=2)=[CH:35][CH:34]=1)=[O:31])=[O:23])[CH:15]([CH3:17])[CH3:16])=[O:13])([O:6]CC)=[O:5])[CH3:2].Br[Si](C)(C)C.C(Cl)(Cl)Cl>O>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][C:12]([N:14]([CH2:18][C:19]1[CH:20]=[C:21]([CH:54]=[CH:55][CH:56]=1)[C:22]([NH:24][C:25]1[S:26][C:27]2[CH2:53][CH2:52][CH2:51][CH2:50][C:28]=2[C:29]=1[C:30]([NH:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][C:44]([C:45]([OH:47])=[O:46])=[CH:48][CH:49]=2)=[CH:37][CH:38]=1)=[O:31])=[O:23])[CH:15]([CH3:17])[CH3:16])=[O:13])([OH:6])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 76113BromotrimethylsilaneHCID 90370293HCID 90370293, compound

Product 1

HCID 90370288HCID 90370288, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 180 mg of 4-[2-(4-{[(2-{[3-({[4-(diethoxyphosphoryl)butanoyl](isopropyl)amino}methyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoic acid, 0.040 mL of bromotrimethylsilane, and 3.6 mL of chloroform was stirred overnight at room temperature. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography, thereby obtaining 42 mg of 4-(2-{4-[({2-[(3-{[{4-[ethoxy(hydroxy)phosphoryl]butanoyl}(isopropyl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoic acid.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f33228c00eb4460a8c221f1a01f74f26
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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