L-Norvaline → (2S,3S)-3-Amino-N-cyclopropyl-2-hydroxy-N-methylhexanamide

HRID 1025316Notes

Reaction equation

N[C@@H](CC)[C@H](O)[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].[NH2:13][C@@H:14]([CH2:18][CH2:19][CH3:20])[C:15]([OH:17])=O.[CH3:21]NC1CC1>>[NH2:13][C@@H:14]([CH2:18][CH2:19][CH3:20])[C@H:15]([OH:17])[C:4]([N:6]([CH:7]1[CH2:9][CH2:8]1)[CH3:21])=[O:5]

Participants

Reactant 3

HCID 65098L-Norvaline

HCID 11029756N-Methylcyclopropanamine

HCID 57872123(2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide

Product 1

HCID 86762427(2S,3S)-3-Amino-N-cyclopropyl-2-hydroxy-N-methylhexanamide

Procedure

The title compound was prepared in analogy to (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide, Representative Procedure B, using (S)-2-aminopentanoic acid in the first step (step B1), and N-methylcyclopropanamine in the seventh step (step B7).

Sources & evidence

ORD record: ord-d3de8b7588684163bc7b4824cf798d33
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729061B2

Reaction notes

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