Dicyclohexylcarbodiimide → HCID 131632219, compound

HRID 1759760Notes

Reaction equation

HRID 1759760 reaction equation
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:22](O)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:55][CH2:56][C:57]([O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58]>CN(C)C=O.S(C1C=CC(C)=CC=1)([O-])(=O)=O.C(N(CC)CC)C>[NH:1]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:22]([NH:55][CH2:56][C:57]([O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 409140Benzyl glycinateHCID 13943016N-(tert-Butoxycarbonyl)glycyl-L-phenylalanyl-L-leucine

Product 1

HCID 131632219HCID 131632219, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolventHCID 85570p-ToluenesulfonateSolvent

Conditions

Temperature
4 °C

Procedure

The Boc-Gly-Phe-Leu-OH obtained in Example 18 (2.4 g) and N-hydroxysuccinimide (656 mg) were dissolved in N,N-dimethylformamide (50 ml), cooled to 4° C., and then added with N,N′-dicyclohexylcarbodiimide (1.17 g) and stirred for 2 hours. To this solution, a N,N-dimethylformamide solution (40 ml), in which tosylate of H-Gly-OBzl (1.9 g) and triethylamine (0.79 ml) had been dissolved, was added and the mixture was allowed to react with stirring at room temperature for 16 hours. This reaction mixture was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=50:1 solution) to give the title compound (2.0 g).

Workup

  1. additionwas added
  2. customto react
  3. stirringwith stirring at room temperature for 16 hours
  4. customThis reaction mixture was evaporated to dryness under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=50:1 solution)

Sources & evidence

ORD record
ord-e1fd359d9aaa4b3a848573292dc1ba70
Source dataset
uspto-grants-2005_01
Patent number
US06838450B2

Reaction notes

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