Sarcosine → Coumarine 3-carboxamide, N-metoxycarbonylmethyl-
Reaction equation
C[NH:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]([C:10]1[C:11](=[O:20])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:9])=O.Cl.[CH3:22]N(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:22][O:6][C:4](=[O:5])[CH2:3][NH:2][C:7]([C:10]1[C:11](=[O:20])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a round bottom flask containing methyl-glycine (89 mg, 1.00 mmol), 3-carboxy coumarine, anh. DCM (25 ml), under Ar, N′-(3 dimethylaminopropyl)-N-ethyl-carbodiimide hydrochloride (EDC) (479 mg, 2.50 mmol) and DMAP (489 mg, 4.00 mmol) were added at room temperature. The resulting mixture was stirred for 1 h 30 min (total conversion was observed by TLC). Then, DCM (20 ml) was added and the solution was washed successively with aq. NaHCO3 (10 ml, sat) and brine (10 ml). The organic phase was dried (Na2SO4), filtered and concentrated. The resulting orange solid obtained was purified by flash LC (silica gel, grad hex:EtOAc 1:1 to 2:1) to give the title compound (445 mg, quant) as a colourless oil. Rf=0.08 (Hex/EtOAc 1:1).
Workup
- washthe solution was washed successively with aq. NaHCO3 (10 ml, sat) and brine (10 ml)
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe resulting orange solid obtained
- customwas purified by flash LC (silica gel, grad hex:EtOAc 1:1 to 2:1)
Sources & evidence
- ORD record
- ord-2bf35b8cf76c4570ab0bf1f15b301ed4
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678765B2
Reaction notes
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