Diethyl Ether → HCID 178455970, compound

HRID 2058122Notes

Reaction equation

HRID 2058122 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]([O:49][C:50]([NH:52][C@H:53]([C:58](O)=[O:59])[C@H:54]([CH2:56][CH3:57])[CH3:55])=[O:51])([CH3:48])([CH3:47])[CH3:46].CCOCC>CN(C=O)C>[C:45]([O:49][C:50]([NH:52][C@H:53]([C:58]([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:59])[C@H:54]([CH2:56][CH3:57])[CH3:55])=[O:51])([CH3:46])([CH3:48])[CH3:47]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 178429589HCID 178429589, compound

Product 1

HCID 178455970HCID 178455970, compoundYield 86.3%

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 the N-hydroxysuccinimide ester of tert-butyloxycarbonyl-L-isoleucine (75.4 mg, 0.23 mM) was added thereto. This mixture was stirred for 3 days at room temperature. To this mixture excess ether was added and the produced precipitate was separated by filtration and dried. This material was dissolved in methyl alcohol (2 ml), and ether (20 ml) was added thereto for reprecipitation to give 7-(Nα -tert-butyloxycarbonyl-L-isoleucyl-L-glutamylglycyl-L-arginyl)amino-4-methylcoumarin [VII] (120 mg, yield: 86.3%).

Workup

  1. temperaturecooling
  2. stirringThis mixture was stirred for 3 days at room temperature
  3. customthe produced precipitate was separated by filtration
  4. customdried
  5. dissolutionThis material was dissolved in methyl alcohol (2 ml)
  6. additionether (20 ml) was added
  7. customfor reprecipitation

Sources & evidence

ORD record
ord-e047f53a9d9b4d52bcbb7970e931eb9f
Source dataset
uspto-grants-1980_07
Patent number
US04215047

Reaction notes

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