Butyl isocyanide → (2S,3S)-3-Amino-N-butyl-2-hydroxyhexanamide dihydrochloride

HRID 1025308

Reaction equation

[ClH:1].Cl.N[C@@H](CC)[C@H](O)[C:6]([NH:8][CH:9]1[CH2:11][CH2:10]1)=[O:7].[NH2:15][C@@H:16]([CH2:19][CH2:20][CH3:21])[CH2:17][OH:18].[N+](CCCC)#[C-:23]>>[ClH:1].[ClH:1].[NH2:15][C@@H:16]([CH2:19][CH2:20][CH3:21])[C@H:17]([OH:18])[C:6]([NH:8][CH2:9][CH2:11][CH2:10][CH3:23])=[O:7]

Participants

Reactant 3

HCID 76008Butyl isocyanide

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

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

Product 1

HCID 86762413(2S,3S)-3-Amino-N-butyl-2-hydroxyhexanamide dihydrochloride

Procedure

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

Sources & evidence

ORD record: ord-97f5da1cfd2547dfbd322d83831b88f6
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729061B2

Linked notes

Loading…