D-Serine → HCID 24798226, compound

HRID 492071Notes

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])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[C:8]([O:16][CH2:17][CH2:18][O:19][C:20]([NH:1][C@H:2]([CH2:3][OH:4])[C:5]([OH:7])=[O:6])=[O:21])(=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618760HCID 86618760, compound

Product 1

HCID 24798226HCID 24798226, compoundYield 70%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (0.509 g, 4.8 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl heptanoate (1 g, 4.03 mmol) were reacted to provide 0.683 g (70% yield) of the title compound (36) as a colorless liquid after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.81 (q, 1H), 5.9 (t, 1H), 4.4 (br s, 1H), 4.14-3.98 (m, 2H), 2.36 (t, 2H), 1.63 (t, 2H), 1.5 (d, 3H), 1.3 (m, 6H), 0.85 (t, 3H). MS (ESI) m/z 327.97 (M+Na)+; 304.00 (M−H)−.

Workup

customwere reacted

Sources & evidence

ORD record: ord-e56fcd5c0cb240adbc14a39e837db2b5
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531572B2

Reaction notes

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