D-Serine → HCID 86618769, compound

HRID 492069Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH3:8][CH:9]([CH3:25])[C:10]([O:12][CH2:13][O:14][C:15](ON1C(=O)CCC1=O)=[O:16])=[O:11]>>[OH:4][CH2:3][C@@H:2]([NH:1][C:15]([O:14][CH2:13][O:12][C:10](=[O:11])[CH:9]([CH3:25])[CH3:8])=[O:16])[C:5]([OH:7])=[O:6]

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618758HCID 86618758, compound

Product 1

HCID 86618769HCID 86618769, compoundYield 35%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (161 mg, 1.5 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)methyl 2-methylpropanoate (330 mg, 1.3 mmol) were reacted to provide 110 mg (35% yield) of the title compound (32) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.61 (br s, 1H), 6.51 (d, 1H), 5.65 (m, 2H), 4.41 (m, 1H), 4.02 (m, 1H), 3.84 (m, 1H), 2.59 (m, 1H), 1.09 (d, 6H). MS (ESI) m/z 250.15 (M+H)+; 267.17 (M+NH4)+; 272.13 (M+Na)+; 248.12 (M−H)−.

Workup

customwere reacted

Sources & evidence

ORD record: ord-41d972c9da534386972d4950a2753740
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531572B2

Reaction notes

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