D-Serine → HCID 86618765, compound

HRID 1715475Notes

Reaction equation

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

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618766HCID 86618766, compound

Product 1

HCID 86618765HCID 86618765, compoundYield 40.3%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (252 mg, 2.4 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2-methylpropanoate (546 mg, 2.0 mmol) were reacted to provide 212 mg (40% yield) of the title compound (29) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.79 (m, 1H), 6.03 (t, 0.2H), 5.58 (br s, 1H), 4.41 (m, 1H), 4.05 (m, 1H), 3.94 (m, 1H), 2.57 (m, 1H), 1.48 (2d, 3H), 1.19 (2d, 6H). MS (ESI) nm/z 281.11 (M+NH4)+; 286.11 (M+Na)+; 262.12 (M−H)−.

Workup

customwere reacted

Sources & evidence

ORD record: ord-44a73d9f4083431fbf6495c649be57bc
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799829B2

Reaction notes

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