Sarcosine → HCID 24798502, compound

HRID 492076Notes

Reaction equation

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

Participants

Reactant 2

HCID 1088Sarcosine

HCID 86618768HCID 86618768, compound

Product 1

HCID 24798502HCID 24798502, compoundYield 53.5%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, sarcosine (0.104 g, 1.1 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl pentanoate (0.268 g, 0.93 mmol) were reacted to provide 0.130 g (53.3% yield) of the title compound (43) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CD3OD, 400 MHz): δ=6.79 (q, 1H), 4.12 (m, 2H), 3.0 (2s, 2H), 2.36 (m, 2H), 1.62 (q, 2H), 1.56 (2d, 3H), 1.39 (q, 2H), 0.97 (t, 3H). MS (ESI) m/z 284.09 (M+Na)+; 260.05 (M−H)−.

Workup

customwere reacted

Sources & evidence

ORD record: ord-d428f46398dd4399ab532a8968b13630
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531572B2

Reaction notes

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