Isopropylamine → (2S,3S)-3-Amino-2-hydroxy-N-isopropylhexanamide

Reaction equation

[NH2:1][C@@H:2]([CH2:11][CH3:12])[C@H:3]([OH:10])[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].N[C@@H:14](CCC)C(O)=O.C(N)(C)C>>[NH2:1][C@@H:2]([CH2:11][CH2:12][CH3:14])[C@H:3]([OH:10])[C:4]([NH:6][CH:7]([CH3:8])[CH3:9])=[O:5]

Participants

Reactant 3

HCID 6363Isopropylamine

HCID 65098L-Norvaline

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

Product 1

HCID 86762422(2S,3S)-3-Amino-2-hydroxy-N-isopropylhexanamide

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 isopropylamine in the seventh step (step B7).

Sources & evidence

ORD record: ord-a1c0d75f00614a23adcbe92ecc10694a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729061B2

Reaction notes

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