Thiophenol → [4-((R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester hydrochloride

HRID 383113Notes

Reaction equation

HRID 383113 reaction equation
[CH3:1][O:2][C:3](=[O:39])[C@H:4]([CH2:35][CH2:36][S:37][CH3:38])[NH:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C@@H:16]2[CH2:20][S:19][CH2:18][N:17]2C(OC(C)(C)C)=O)=[O:15])=[CH:9][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(S)C=CC=CC=1.[ClH:47].O1CCOCC1>>[ClH:47].[CH3:1][O:2][C:3](=[O:39])[C@H:4]([CH2:35][CH2:36][S:37][CH3:38])[NH:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C@@H:16]2[CH2:20][S:19][CH2:18][NH:17]2)=[O:15])=[CH:9][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 7969ThiophenolHCID 204431481,4-Dioxane hydrochlorideHCID 54440271[4-(N-tert-butoxycarbonyl-(R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester

Product 1

HCID 70212058[4-((R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester hydrochloride

Procedure

To a mixture of [4-(N-tert-butoxycarbonyl-(R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester (270 mg, 0.47 mmol) and thiophenol (0.1 mL, 0.97 mmol) was added 4N HCl-dioxane (10 mL) and the reaction mixture was stirred for 45 minutes at ambient temperature. The reaction mixture was partitioned between water and ether. The aqueous phase was extracted with ether. The organic extracts were discarded and the aqueous phase was lyophilized to give [4-((R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester hydrochloride (150 mg).

Workup

  1. customThe reaction mixture was partitioned between water and ether
  2. extractionThe aqueous phase was extracted with ether

Sources & evidence

ORD record
ord-6fede65a9663405fb375dd1ae51b66e7
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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