(2S)-2-(((tert-butoxy)carbonyl)amino)hex-5-enoic acid → (S)-2-((tert-Butoxycarbonyl)(methyl)amino)hex-5-enoic acid

HRID 501673Notes

Reaction equation

HRID 501673 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH:15]=[CH2:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17]C(CCCC)C(N[C@@H](CC=C)C(O)=O)=O>>[C:1]([O:5][C:6]([N:8]([CH3:17])[C@@H:9]([CH2:13][CH2:14][CH:15]=[CH2:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 20765220(2S)-2-(((tert-butoxy)carbonyl)amino)hex-5-enoic acidHCID 86622314(2S)-2-(2-methylhexanamido)pent-4-enoic acid

Product 1

HCID 86622313(S)-2-((tert-Butoxycarbonyl)(methyl)amino)hex-5-enoic acidYield 98%

Procedure

Step K (1): Same procedure as Step D (3). (S)-2-(tert-Butoxycarbonyl-amino)hex-5-enoic acid (was used in place of (2S)-2-(2-methylhexanamido)pent-4-enoic acid. The procedure provided 2.06 g (98% yield) of (S)-2-(tert-butoxycarbonyl(methyl)amino)hex-5-enoic acid. LRMS (M−H)−=242.1; 1H NMR (500 MHz, CDCl3) δ ppm 1.45 (d, J=15.26 Hz, 9H) 1.86 (s, 1H) 1.99-2.19 (m, 3H) 2.82 (d, J=18.01 Hz, 3H) 4.36-4.72 (m, 1H) 4.96-5.12 (m, 2H) 5.71-5.87 (m, 1H).

Sources & evidence

ORD record
ord-e423bac2a5364dcd9b53234bf99cf42f
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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