2-Pentyl isocyanide → (2S,3S)-3-Amino-2-hydroxy-N-(pentan-2-yl)hexanamide dihydrochloride

Reaction equation

[ClH:1].Cl.N[C@@H](CC)[C@H](O)C(NC1CC1)=[O:7].[NH2:15][C@@H:16]([CH2:19][CH2:20][CH3:21])[CH2:17][OH:18].[N+:22]([CH:24]([CH2:26][CH2:27][CH3:28])[CH3:25])#[C-:23]>>[ClH:1].[ClH:1].[NH2:15][C@@H:16]([CH2:19][CH2:20][CH3:21])[C@H:17]([OH:18])[C:23]([NH:22][CH:24]([CH2:26][CH2:27][CH3:28])[CH3:25])=[O:7]

Participants

Reactant 3

HCID 40845582-Pentyl isocyanide

HCID 6951248(2S)-2-aminopentan-1-ol

HCID 86762404(2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide dihydrochloride

Product 1

HCID 86762419(2S,3S)-3-Amino-2-hydroxy-N-(pentan-2-yl)hexanamide dihydrochloride

Procedure

The title compound was prepared in analogy to (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide dihydrochloride, Representative Procedure A, starting with (S)-2-aminopentan-1-ol in the first step (A1), and using 2-isocyanopentane in the third step (A3).

Sources & evidence

ORD record: ord-b299ebf622b94572b576b92d41094a87
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729061B2

Reaction notes

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