Dicyclohexylcarbodiimide → HCID 10412941, compound

HRID 1728379Notes

Reaction equation

HRID 1728379 reaction equation
[CH3:1][C:2]([CH3:34])([O:4][C:5]([C@H:7]([NH:25][C@H:26]([C:31](O)=[O:32])[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:40]=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.CN>C(N(CC)CC)C.ClCCl.O>[CH3:34][C:2]([O:4][C:5](=[O:6])[C@H:7]([NH:25][C@H:26]([C:31]([NH:41][CH3:40])=[O:32])[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])([CH3:3])[CH3:1]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 6364545Methylamine hydrochlorideHCID 54449037HCID 54449037, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 10412941HCID 10412941, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

300 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 120 mg of hydroxybenzotriazol.H2O, 150 mg of dicyclohexylcarbodiimide, 600 mg methylamine-hydrochoride, and 30 mL dichloromethane. 0.5 ; mL triethylamine was added and the mixture was stirred for 18 h. The mixture was filtered through celite and the solvent was removed by evaporation. The resulting residue was purified by silica chromatography using hexane:ethyl acetate:dichloromethane (2:1:1) as eluent to give the title compound as a white solid; 320 mg.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was removed by evaporation
  3. customThe resulting residue was purified by silica chromatography

Sources & evidence

ORD record
ord-7602fea2613f4b0490d7e322cf49cb24
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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