D-Leucine, methyl ester → (R)-methyl 2-(4-fluoro-3-methylbenzamido)-4-methylpentanoate

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][C:14](=[O:21])[C@@H:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[NH2:16]>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][C@H:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([O:13][CH3:12])=[O:21])=[O:8])=[CH:4][C:3]=1[CH3:11]

Participants

Reactant 2

HCID 89967D-Leucine, methyl ester

HCID 2428284-Fluoro-3-methylbenzoic acid

Product 1

HCID 57527876(R)-methyl 2-(4-fluoro-3-methylbenzamido)-4-methylpentanoate

Procedure

Prepared in a similar manner to example 4 using 4-fluoro-3-methylbenzoic acid and D-leucine methyl ester. MS (M+H, 282).

Sources & evidence

ORD record: ord-42be34b6d484487ba5f92572a66bc7d1
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895050B2

Reaction notes

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