Sarcosine → Coumarine 3-carboxamide, N-metoxycarbonylmethyl-

HRID 1394005Notes

Reaction equation

HRID 1394005 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.[CH2:21](Cl)Cl>CN(C1C=CN=CC=1)C>[CH3:21][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

5

Reactant 3

HCID 1088SarcosineHCID 6344Dichloromethane2×HCID 10752Coumarin-3-Carboxylic Acid

Product 1

HCID 599285Coumarine 3-carboxamide, N-metoxycarbonylmethyl-

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

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 Dimethylaminopropil)-N-ethyl-carbodiimid hydrochlorid (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

  1. washthe solution was washed successively with aq. NaHCO3 (10 ml, sat) and brine (10 ml)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting orange solid obtained
  6. customwas purified by flash LC (silica gel, grad hex:EtOAc 1:1 to 2:1)

Sources & evidence

ORD record
ord-b1b71138861e4b68ba45ad6b11f037d7
Source dataset
uspto-grants-2008_03
Patent number
US07348310B2

Reaction notes

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