Dicyclohexylcarbodiimide → HCID 10394325, compound

HRID 1728385Notes

Reaction equation

HRID 1728385 reaction equation
[CH3:1][C:2]([CH3:34])([O:4][C:5]([C@H:7]([NH:25][C@H:26]([C:31]([OH:33])=O)[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[CH:16]=[C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]3=[CH:13][C:12]=2[C:11]1=[O:24])=[O:6])[CH3:3].OC1C2N=N[NH:41]C=2C=CC=1.NC[CH2:47][C:48]1[CH:53]=[CH:52][C:51]([S:54]([NH2:57])(=[O:56])=[O:55])=[CH:50][CH:49]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.O.CN(C=O)C>[CH3:3][C:2]([O:4][C:5](=[O:6])[C@H:7]([NH:25][C@H:26]([C:31]([NH:41][CH2:47][C:48]1[CH:53]=[CH:52][C:51]([S:54](=[O:56])(=[O:55])[NH2:57])=[CH:50][CH:49]=1)=[O:33])[CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:8][CH2:9][N:10]1[C:11](=[O:24])[C:12]2[CH:13]=[C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]3=[CH:16][C:17]=2[C:18]1=[O:19])([CH3:34])[CH3:1]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 54449037HCID 54449037, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 10394325HCID 10394325, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

100 mg of N-[(R)-1-[(1,1-dimethylethoxy)carbonyl]-3-(1,3-dihydro-1,3-dioxo-2H-benz[f]isoindol-2-yl)propyl]-L-leucine, prepared as in Example L, was added to 0.8 mL DMF. 39 mg of hydroxybenzotriazol.H2O was added to the mixture followed by 57 mg of 4-aminoethylbenzenesulfonamide, 0.03 mL of N-methyl-4-morpholine, and 53 mg of dicyclohexylcarbodiimide. The mixture was stirred 72 h, and diluted with dichloromethane. The solvents were removed by evaporation and the resulting solid was purified by reverse phase H.P.L.C. The solvents were removed by lyopholization to give the title compound as a white solid; 104 mg.

Workup

  1. customThe solvents were removed by evaporation
  2. customthe resulting solid was purified by reverse phase H.P.L.C
  3. customThe solvents were removed by lyopholization

Sources & evidence

ORD record
ord-f6a2b2f1f9874c4d9258a8d0a9086274
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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