Methanol → HCID 178429591, compound

HRID 2058118Notes

Reaction equation

HRID 2058118 reaction equation
[ClH:1].[C:2]([NH:12][C@H:13]([C:21]([OH:23])=O)[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:20])[NH2:19])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([CH3:36])=[CH:30][C:31](=[O:35])[O:32]2)=[CH:27][CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1.CO>CN(C)C=O>[ClH:1].[C:2]([NH:12][C@H:13]([C:21]([NH:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([CH3:36])=[CH:30][C:31](=[O:35])[O:32]2)=[CH:27][CH:26]=1)=[O:23])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:20])[NH2:19])([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 922497-Amino-4-methylcoumarinHCID 178479461HCID 178479461, compound

Product 1

HCID 178429591HCID 178429591, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Nα -carbobenzoxy-L-arginine hydrochloric acid salt (69.0 g, 0.2 M) and 7-amino-4-methylcoumarin (17.5 g, 0.1 M) were dissolved in dimethylformamide (DMF) (300 ml). Dicyclohexylcarbodiimide (DCCD) (21 g, 0.1 M) was added to the mixture with stirring at room temperature. This mixture was stirred overnight at room temperature, and the produced dicyclohexyl urea was removed by filtration. The obtained filtrate was concentrated under reduced pressure and to the thus obtained residue methyl alcohol (50 ml) and ethyl acetate (500 ml) were added. The precipitated material was separated by filtration to give crude crystals (19 g). These crystals were dissolved in a mixture of heated DMF (30 ml) and heated methyl alcohol (100 ml) and insoluble material was removed by filtration. To the filtrate ethyl acetate (400 ml) was added and the thereby precipitated white crystals were separated by filtration and dried to give 7-(Nα -carbobenzoxy-L-arginyl)amino-4-methylcoumarin hydrochloric acid salt (14.5 g, yield: 29%).

Workup

  1. stirringThis mixture was stirred overnight at room temperature
  2. customthe produced dicyclohexyl urea was removed by filtration
  3. concentrationThe obtained filtrate was concentrated under reduced pressure and to the thus obtained residue methyl alcohol (50 ml) and ethyl acetate (500 ml)
  4. additionwere added
  5. customThe precipitated material was separated by filtration
  6. customto give crude crystals (19 g)
  7. customwas removed by filtration
  8. additionTo the filtrate ethyl acetate (400 ml) was added
  9. customthe thereby precipitated white crystals
  10. customwere separated by filtration
  11. customdried

Sources & evidence

ORD record
ord-5bc55d7caaa548348ca1dab6b566877b
Source dataset
uspto-grants-1980_07
Patent number
US04215047

Reaction notes

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