(2S)-2-amino-3-(tert-butoxy)propanoic acid → O-(tert-Butyl)-N-{[(2,2-dimethylhex-5-en-1-yl)oxy]carbonyl}-L-serine

HRID 2377635Notes

Reaction equation

HRID 2377635 reaction equation
CC(C)(C)[C@@H](C(O)=O)N[C:5](OCCCC=C)=[O:6].[C:18]([O:22][CH2:23][C@@H:24]([C:26]([OH:28])=[O:27])[NH2:25])([CH3:21])([CH3:20])[CH3:19].[CH3:29][C:30]([CH3:37])([CH2:33][CH2:34][CH:35]=[CH2:36])[CH2:31][OH:32]>>[C:18]([O:22][CH2:23][C@@H:24]([C:26]([OH:28])=[O:27])[NH:25][C:5]([O:32][CH2:31][C:30]([CH3:37])([CH3:29])[CH2:33][CH2:34][CH:35]=[CH2:36])=[O:6])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 3

HCID 7004940(2S)-2-amino-3-(tert-butoxy)propanoic acidHCID 102408212,2-Dimethylhex-5-en-1-olHCID 453799283-Methyl-N-{[(pent-4-en-1-yl)oxy]carbonyl}-L-valine

Product 1

HCID 45379614O-(tert-Butyl)-N-{[(2,2-dimethylhex-5-en-1-yl)oxy]carbonyl}-L-serine

Procedure

O-(tert-Butyl)-N-{[(2,2-dimethylhex-5-en-1-yl)oxy]carbonyl}-L-serine was prepared according to the procedure for 3-methyl-N-[(pent-4-enyloxy)carbonyl]-L-valine using O-(tert-butyl)-L-serine and 2,2-dimethylhex-5-en-1-ol. 1H NMR (500 MHz, CDCl3, ppm) δ 5.75-5.86 (m, 1 H), 4.90-5.04 (m, 2 H), 4.02 (m, 1 H), 3.57-3.90 (m, 4 H), 1.98-2.05 (m, 2 H), 1.27-1.36 (m, 2 H), 1.14 (s, 9 H), 1.01 (d, J=6.5 Hz, 1 H), and 6.09 (s, 6 H).

Sources & evidence

ORD record
ord-df840d8e5d6345c1a274f3e88199faf6
Source dataset
uspto-grants-2008_12
Patent number
US07470664B2

Reaction notes

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