D-Serine → (2R)-2-[(Cyclohexylcarbonyloxyethoxy)carbonylamino]-3-hydroxypropanoic Acid

HRID 492064Notes

Reaction equation

HRID 492064 reaction equation
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH:8]1([C:14]([O:16][CH2:17][CH2:18][O:19][C:20](ON2C(=O)CCC2=O)=[O:21])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([C:14]([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]1

Participants

3

Reactant 2

HCID 71077D-SerineHCID 86618759(2,5-Dioxoazolidinyloxycarbonyloxy)ethyl cyclohexanecarboxylate

Product 1

HCID 24798220(2R)-2-[(Cyclohexylcarbonyloxyethoxy)carbonylamino]-3-hydroxypropanoic AcidYield 58%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (252 mg, 2.4 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl cyclohexanecarboxylate (626 mg, 2.0 mmol) were reacted to provide 350 mg (58% yield) of the title compound (27) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.79 (m, 1H), 6.05 (t, 1H), 5.45 (br s, 1H), 4.41 (m, 1H), 4.04 (m, 1H), 3.92 (m, 1H), 2.30 (m, 1H), 1.09-1.95 (m, 13H). MS (ESI) m/z 321.13 (M+NH4)+; 326.09 (M+Na)+; 302.06 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2ff5c94d0aae4e81aac176994ed8b25a
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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