D-Serine → HCID 24798222, compound

HRID 1715471Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH3:8][C:9]1[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=1[C:11]([O:13][CH2:14][CH2:15][O:16][C:17](ON1C(=O)CCC1=O)=[O:18])=[O:12]>>[OH:4][CH2:3][C@@H:2]([NH:1][C:17]([O:16][CH2:15][CH2:14][O:13][C:11]([C:10]1[CH:27]=[CH:28][CH:29]=[CH:30][C:9]=1[CH3:8])=[O:12])=[O:18])[C:5]([OH:7])=[O:6]

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618756HCID 86618756, compound

Product 1

HCID 24798222HCID 24798222, compoundYield 33%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (252 mg, 2.4 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2-methylbenzoate (642 mg, 2.0 mmol) were reacted to provide 203 mg (33% yield) of the title compound (25) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=7.85 (br d, 1H), 7.39 (m, 1H), 7.20 (m, 2H), 7.01 (m, 1H), 6.61 (br s, 1H), 6.08 (t, 1H), 4.40 (m, 1H), 4.02 (m, 1H), 3.94 (m, 1H), 2.58 (s, 3H), 1.58 (2d, 3H). MS (ESI) m/z 312.01 (M+H)+; 329.08 (M+NH4)+; 334.06 (M+Na)+.

Workup

customwere reacted

Sources & evidence

ORD record: ord-5306d17d47a541a0805a25de73364426
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799829B2

Reaction notes

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