D-Serine → HCID 24798133, compound

HRID 492067Notes

Reaction equation

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

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618767HCID 86618767, compound

Product 1

HCID 24798133HCID 24798133, compoundYield 48.4%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (252 mg, 2.4 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl butanoate (546 mg, 2.0 mmol) were reacted to provide 255 mg (40% yield) the title compound (30) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.80 (m, 1H), 6.09 (t, 1H), 5.81 (br s, 1H), 4.41 (m, 1H), 4.07 (m, 1H), 3.92 (m, 1H), 2.31 (m, 2H), 1.65 (m, 2H), 1.50 (d, 3H), 0.99 (m, 3H). MS (ESI) m/z 286.07 (M+Na)+; 262.06 (M−H)−.

Workup

customwere reacted

Sources & evidence

ORD record: ord-f9d4ec5a83ea436b97d0d9fbab19fbf5
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531572B2

Reaction notes

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