Formic Acid → HCID 42256969, compound

HRID 1356877Notes

Reaction equation

HRID 1356877 reaction equation
N1CCC[C@H]1C(OC(C)(C)C)=O.CCN(CC)CC.[C:20]1([CH2:26][CH2:27][S:28]([N:31]2[CH2:42][CH2:41][CH2:40][C@H:32]2[C:33]([O:35]C(C)(C)C)=[O:34])(=[O:30])=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)=O>C(Cl)Cl>[C:20]1([CH2:26][CH2:27][S:28]([N:31]2[CH2:42][CH2:41][CH2:40][C@H:32]2[C:33]([OH:35])=[O:34])(=[O:30])=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 131723155HCID 131723155, compound

Product 1

HCID 42256969HCID 42256969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. customto give
  2. customthe mixture was evaporated

Sources & evidence

ORD record
ord-4ec2bb56199640d099230bfe5458159d
Source dataset
uspto-grants-2003_07
Patent number
US06586602B2

Reaction notes

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