D-Serine → HCID 24798132, compound

HRID 1715477Notes

Reaction equation

HRID 1715477 reaction equation
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[C:8]([O:14][CH2:15][CH2:16][O:17][C:18](ON1C(=O)CCC1=O)=[O:19])(=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12]>>[OH:4][CH2:3][C@@H:2]([NH:1][C:18]([O:17][CH2:16][CH2:15][O:14][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:19])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 71077D-SerineHCID 86618768HCID 86618768, compound

Product 1

HCID 24798132HCID 24798132, compoundYield 73%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (504 mg, 4.8 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl pentanoate (1.1 g, 4.0 mmol) were reacted to provide 809 mg (73% yield) of the title compound (31) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.80 (m, 1H), 6.26 (br s, 1H), 5.50 (br s, 1H), 4.40 (m, 1H), 4.02 (m, 1H), 3.85 (m, 1H), 2.36 (m, 2H), 1.60 (m, 2H), 1.47 (d, 3H), 1.37 (m, 2H), 0.91 (t, 3H). MS (ESI) m/z 295.19 (M+NH4)+; 300.08 (M+Na)+; 272.12 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4676572d48244959b6123e5b6a778870
Source dataset
uspto-grants-2010_09
Patent number
US07799829B2

Reaction notes

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