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

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.[CH3:13][O:14][C:15](=[O:22])[C@@H:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH2:17]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:17][C@H:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:15]([O:14][CH3:13])=[O:22])=[O:7]

Participants

Reactant 2

HCID 89967D-Leucine, methyl ester

HCID 27334013-Fluoro-4-methoxybenzoic acid

Product 1

HCID 32044601(R)-methyl 2-(3-fluoro-4-methoxybenzamido)-4-methylpentanoate

Procedure

Prepared in a similar manner to example 4 using 3-fluoro-4-methoxybenzoic acid and D-leucine methyl ester. MS (M+H, 298).

Sources & evidence

ORD record: ord-828a6c980fb84500a3385c0d9b1942cb
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895050B2

Reaction notes

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