Boc-L-methioninol → (2RS,3S)-N-cyclopentyl-3-amino-2-hydroxy-5-(methylthio)pentanamide

HRID 1953436Notes

Reaction equation

HRID 1953436 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]([CH2:27][CH2:28][S:29][CH3:30])[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])[CH2:27][CH2:28][S:29][CH3:30])[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 10988238Boc-L-methioninolHCID 13969856(S)-tert-butyl 1-hydroxyhexan-2-ylcarbamate

Product 1

HCID 53684029(2RS,3S)-N-cyclopentyl-3-amino-2-hydroxy-5-(methylthio)pentanamideYield 42%

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 7.53 g of (S)-2-[N-(2-methyl-2-propyloxycarbonyl) amino]-4-(methylthio)butanol, whereby 3.22 g of the captioned (2RS,3S)-N-cyclopentyl-3-amino-2-hydroxy-5-(methylthio)pentanamide was obtained in a yield of 42%.

Workup

  1. customThe same reaction procedure as in Reference Example 12

Sources & evidence

ORD record
ord-6b3342bd5fdd458eaae0966cf7fcb9bf
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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