D-Serine → HCID 24798223, compound

HRID 492061Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH3:8][C:9]([CH3:27])([CH3:26])[C:10]([O:12][CH2:13][CH2:14][O:15][C:16](ON1C(=O)CCC1=O)=[O:17])=[O:11]>>[CH3:8][C:9]([CH3:27])([CH3:26])[C:10]([O:12][CH2:13][CH2:14][O:15][C:16]([NH:1][C@H:2]([CH2:3][OH:4])[C:5]([OH:7])=[O:6])=[O:17])=[O:11]

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618763HCID 86618763, compound

Product 1

HCID 24798223HCID 24798223, compoundYield 28%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (504 mg, 4.8 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2,2-dimethylpropanoate (1.1 g, 4.0 mmol) were reacted to provide 305 mg (28% yield) of the title compound (24) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.78 (m, 1H), 6.40 (br s, 1H), 6.11 (t, 1H), 4.41 (m, 1H), 4.04 (m, 1H), 3.93 (m, 1H), 1.44 (2d, 3H), 1.20 (s, 9H). MS (ESI) m/z 278.05 (M+H)+; 295.06 (M+NH4)+; 300.04 (M+Na)+; 276.04 (M−H)−.

Workup

customwere reacted

Sources & evidence

ORD record: ord-29dc4e99da5c4091b13a63941cdaa154
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531572B2

Reaction notes

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