HCID 131723156, compound → HCID 69977669, compound

HRID 1356878Notes

Reaction equation

HRID 1356878 reaction equation
C1([CH2:7][CH2:8][S:9]([N:12]2[CH2:34][CH2:33][CH2:32][C@H:13]2[C:14]([NH:16][C@H:17]([C:25]([O:27]C(C)(C)C)=[O:26])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])(=[O:11])=[O:10])C=CC=CC=1>C(O)=O>[C:19]1([CH:8]([S:9]([N:12]2[CH2:34][CH2:33][CH2:32][C@H:13]2[C:14]([NH:16][C@H:17]([C:25]([OH:27])=[O:26])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])(=[O:10])=[O:11])[CH3:7])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 131723156HCID 131723156, compound

Product 1

HCID 69977669HCID 69977669, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

PhCH2CH2SH was treated with Cl2 in a rapidly stirred mixture of CHCl3 and H2O, and then the CHCl3 layer was washed with 5% NaHSO3 and sat. NaCl, dried with MgSO4, filtered, and concentrated to give PhCH2CH2SO2Cl. This product was treated with Pro-OtBu and Et3N in CH2Cl2 to give, after aqueous workup, PhCH2CH2SO2-Pro-OtBu. This product was treated with HCO2H, and the mixture was evaporated to give PhCH2CH2SO2-Pro-OH. This product was treated with HCl.Phe-OtBu, EDAC, HOBT, and Et3N in CH2Cl2 to give, after aqueous workup and flash chromatography, PhCH2CH2SO2-Pro-Phe-OtBu. This product was treated with HCO2H, and the mixture was evaporated to give the title compound as a clear oil.

Workup

  1. customthe mixture was evaporated

Sources & evidence

ORD record
ord-f47bd13e81ad43a791a673e7406fd100
Source dataset
uspto-grants-2003_07
Patent number
US06586602B2

Reaction notes

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