Diethyl Ether → HCID 178475070, compound

HRID 2058121Notes

Reaction equation

HRID 2058121 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]([C:23]([NH:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30]([CH3:37])=[CH:31][C:32](=[O:36])[O:33]2)=[CH:28][CH:27]=1)=[O:24])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:22])[NH2:21])=[O:13])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].C(N(CC)CC)C.[C:45](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:47])[CH3:46].CCOCC>CN(C=O)C>[C:45]([NH:1][C@H:2]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]([C:23]([NH:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30]([CH3:37])=[CH:31][C:32](=[O:36])[O:33]2)=[CH:28][CH:27]=1)=[O:24])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:21])[NH2:22])=[O:13])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7])(=[O:47])[CH3:46]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 132434-Nitrophenyl AcetateHCID 178429589HCID 178429589, compound

Product 1

HCID 178475070HCID 178475070, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(L-glutamylglycyl-L-arginyl)amino-4-methyl-coumarin (100 mg, 0.18 mM) was dissolved in DMF (2 ml), and triethylamine (0.03 ml) was added thereto with stirring and cooling. This mixture was adjusted to pH about 7, and then p-nitrophenyl acetate (36.1 mg, 0.23 mM) was added thereto. This mixture was stirred for 2 days at room temperature. Excess ether was added to the mixture and the produced precipitate was separated by filtration and dried. This product was dissolved in 80% methyl alcohol (2 ml) and ethyl acetate (30 ml) was added thereto for re-precipitation to give 7-(Nα -acetyl-L-glutamylglycyl-L-arginyl)amino-4-methylcoumarin [VI] (99 mg, yield: 84.9%).

Workup

  1. temperaturecooling
  2. stirringThis mixture was stirred for 2 days at room temperature
  3. customthe produced precipitate was separated by filtration
  4. customdried
  5. dissolutionThis product was dissolved in 80% methyl alcohol (2 ml)
  6. additionethyl acetate (30 ml) was added
  7. customfor re-precipitation

Sources & evidence

ORD record
ord-b44a55f47fd54a07b9bee269c61ad66e
Source dataset
uspto-grants-1980_07
Patent number
US04215047

Reaction notes

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