2-Amino-4-chlorobenzenethiol → Methyl beta-[(2-amino-4-chlorophenyl)thio]-N-[(benzyloxy)carbonyl]phenylalaninate

HRID 1593277Notes

Reaction equation

HRID 1593277 reaction equation
[CH2:1]([O:8][C:9]([NH:11]/[C:12](=[CH:17]\[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)/[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[C:27]([NH2:32])[CH:26]=1>C(OCC)(=O)C>[NH2:32][C:27]1[CH:26]=[C:25]([Cl:24])[CH:30]=[CH:29][C:28]=1[S:31][CH:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C@@H:12]([C:13]([O:15][CH3:16])=[O:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

4

Reactant 2

HCID 120002-Amino-4-chlorobenzenethiolHCID 14861157HCID 14861157, compound

Product 1

HCID 68604058Methyl beta-[(2-amino-4-chlorophenyl)thio]-N-[(benzyloxy)carbonyl]phenylalaninateYield 28%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using a procedure similar to that described in Example 10, part b, except using methyl (2Z)-2-{[(benzyloxy)carbonyl]amino}-3-phenylacrylate (9a) (4.0 g, 12.9 mmol) as the olefin component, and 4-chloro-2-aminothiophenol (10 g, 62.7 mmol) as the thiol component (stirred for 6 days), the product was obtained as a crude oil. Flash column chromatography (5:1 hexanes:ethyl acetate) returned the title compound (1.7 g, 28%). Recrystallization from ethyl acetate-hexanes afforded the title compound (13a) (1.4 g) as a white solid (>98% erythro). MS APCI, m/z=471 (M+1). LC/MS: 2.90 min.

Workup

  1. customthe product was obtained as a crude oil

Sources & evidence

ORD record
ord-8ccf7528a9c447019e5e5e9a6e1e2a2b
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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