N-[tert-butoxycarbonyl]-L-serine → N-[(1,1-Dimethylethoxy)carbonyl]-O-methyl-L-homoserine

HRID 2107869Notes

Reaction equation

HRID 2107869 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][CH2:11][OH:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:16](N[C@H](C(O)=O)CO)(OC(C)(C)C)=O>>[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][CH2:11][O:12][CH3:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

3

Reactant 2

HCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 13066457(2S)-2-(((tert-butoxy)carbonyl)amino)-4-hydroxybutanoic acid

Product 1

HCID 15058461N-[(1,1-Dimethylethoxy)carbonyl]-O-methyl-L-homoserine

Procedure

Boc-homoserine (0.51 g) was methylated as described for Boc-serine in Example 73. This afforded 0.45 g crude product which was carried on without further purification. NMR (300 MHz, CDCl3) delta 1.40 (s, 9H), 3.16 (s, 3H), 3.90 (m, 2H).

Workup

  1. customThis afforded 0.45 g crude product which was carried on without further purification

Sources & evidence

ORD record
ord-cdd7acd4b1954eb9a54b15b05bc233cb
Source dataset
uspto-grants-1990_06
Patent number
US04935405

Reaction notes

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