1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate → (2RS,3S)-N-cyclopentyl-3-amino-2-hydroxybutanamide

HRID 1953437Notes

Reaction equation

HRID 1953437 reaction equation
CC(O[C:6]([NH:8][C@@H:9]([CH2:12][CH2:13][CH2:14][CH3:15])CO)=[O:7])(C)C.CC(OC([NH:23][C@@H:24]([CH3:27])[CH2:25][OH:26])=O)(C)C>>[CH:9]1([NH:8][C:6](=[O:7])[CH:25]([OH:26])[C@@H:24]([NH2:23])[CH3:27])[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 13969856(S)-tert-butyl 1-hydroxyhexan-2-ylcarbamate

Product 1

HCID 54338658(2RS,3S)-N-cyclopentyl-3-amino-2-hydroxybutanamideYield 45%

Procedure

The same reaction procedure as in Reference Example 12 was repeated except that (S)-2-[N-(2-methyl-2-propyloxycarbonyl)amino]hexanol used in Reference Example 12 was replaced by 14.33 g of (S)-2-[N-(2-methyl-2-propyloxycarbonyl) amino]propanol, whereby 6.95 g of the captioned (2RS,3S)-N-cyclopentyl-3-amino-2-hydroxybutanamide was obtained in a yield of 45%. 1H-NMR (CDCl3, δ): 1.05 (3/2H, d, J=7 Hz), 1.15 (3/2H, d, J=7 Hz), 1.35-1.50 (2H, m), 1.55-1.76 (4H, m), 1.90-2.10 (2H, m), 3.31-3.41 (1/2H, m), 3.48-3.52 (1/2H, m), 3.74 (1/2H, d, J=3 Hz), 3.87 (1/2H, d, J=5 Hz), 4.13-4.29 (1H, m), 7.18 (1/2H, d, J=8 Hz), 7.25 (1/2H, d, J=8 Hz).

Workup

  1. customThe same reaction procedure as in Reference Example 12

Sources & evidence

ORD record
ord-1e0cb8675d1a42b0b25b65ee546a80c2
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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