Hydrochloric Acid → HCID 69429673, compound

HRID 1006800Notes

Reaction equation

HRID 1006800 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:23][N:24]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])=O)(C)(C)C.Cl>CCOC(C)=O>[C:38]([O:37][C:35](=[O:36])[CH2:34][N:24]([CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])[CH2:23][C@@H:9]1[CH2:10][C@@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:12][NH:8]1)([CH3:41])([CH3:39])[CH3:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69433324HCID 69433324, compound

Product 1

HCID 69429673HCID 69429673, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

397 mg (0.67 mmol) (2S,4R)-2-[[tert-butoxycarbonylmethyl-(2,5-difluoro-benzyl)-amino]-methyl]-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester were treated with 4.2 ml 1N HCl in EtOAc at RT. The reaction mixture was concentrated and tituration with ether yielded 250 mg (76%) (2S,4R)-[(2,5-difluoro-benzyl)-[4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl]-amino]-acetic acid tert-butyl ester as light brown solid, which was transformed to (2S,4R)-2-[[tert-butoxycarbonylmethyl-(2,5-difluoro-benzyl)-amino]-methyl]-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid butyl ester according to example 4b by treatment with butyl chloroformate.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-fd0672c670944c3ca932c4b3a6b467eb
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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