D-Serine → HCID 24798219, compound

HRID 492065Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[C:8]([O:16][CH2:17][CH2:18][O:19][C:20](ON1C(=O)CCC1=O)=[O:21])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[OH:4][CH2:3][C@@H:2]([NH:1][C:20]([O:19][CH2:18][CH2:17][O:16][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:15])=[O:21])[C:5]([OH:7])=[O:6]

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618757HCID 86618757, compound

Product 1

HCID 24798219HCID 24798219, compoundYield 69%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (252 mg, 2.4 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl benzoate (614 mg, 2.0 mmol) were reacted to provide 410 mg (69% yield) the title compound (28) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=8.00 (m, 2H), 7.55 (m, 1H), 7.40 (m, 2H), 7.01 (m, 1H), 6.59 (br s, 1H), 6.21 (m, 1H), 4.39 (m, 1H), 4.02 (m, 1H), 3.86 (m, 1H), 1.60 (2d, 3H). MS (ESI) m/z 298.10 (M+H)+; 315.11 (M+NH4)+; 320.07 (M+Na)+.

Workup

customwere reacted

Sources & evidence

ORD record: ord-183cfd088c8d459abe9c8b1ac3aff9ac
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531572B2

Reaction notes

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