Sarcosine → HCID 24798588, compound

HRID 1715489Notes

Reaction equation

HRID 1715489 reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].[C:7]([O:15][CH:16]([O:20][C:21](ON1C(=O)CCC1=O)=[O:22])[CH:17]([CH3:19])[CH3:18])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(#N)C.O>[CH3:2][N:1]([C:21]([O:20][CH:16]([O:15][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:14])[CH:17]([CH3:19])[CH3:18])=[O:22])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 1088SarcosineHCID 86610294HCID 86610294, compound

Product 1

HCID 24798588HCID 24798588, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Following the general procedure for the synthesis of acyloxyalkylcarbamates, sarcosine (0.345 g, 3.8 mmols) and 1-(2,5-dioxoazolidinyloxycarbonyloxy)-2-methylpropyl benzoate (1 g, 2.98 mmol) were reacted in an acetonitrile/water mixture (20 mL) to provide 0.364 g (39.5% yield) of the title compound (48) as a colorless, waxy material after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=8.05 (t, 2H), 7.59 (t, 1H), 7.43 (t, 2H), 6.84 (m, 1H), 4.21-3.88 (br m, 2H), 3.0 (d, 3H), 2.25 (m, 1H), 1.15 (dd, 6H). MS (ESI) m/z 332.20 (M+Na)+; 308.21 (M−H)−.

Sources & evidence

ORD record
ord-ce4578dc3df443d0951285453c6b8b33
Source dataset
uspto-grants-2010_09
Patent number
US07799829B2

Reaction notes

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