Dicyclohexylcarbodiimide → HCID 178445941, compound

HRID 1728381Notes

Reaction equation

HRID 1728381 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].ONC(=O)CCC(N)=O.C1(N=C=NC2CCCCC2)CCCCC1.Cl.Cl.[NH:61]1[C:65]([CH2:66][NH2:67])=[N:64][N:63]=[N:62]1>CN(C=O)C.C(N(CC)CC)C>[CH3:3][C:2]([O:4][C:5](=[O:6])[C@H:7]([NH:25][C@H:26]([C:31]([NH:67][CH2:66][C:65]1[NH:64][N:63]=[N:62][N:61]=1)=[O:33])[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])([CH3:1])[CH3:34]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 18381240N-hydroxysuccinamideHCID 54449037HCID 54449037, compoundHCID 178478689HCID 178478689, compound

Product 1

HCID 178445941HCID 178445941, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

50 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 of 40 mg N-hydroxysuccinamide in 5 mL DMF. 150 mg of dicyclohexylcarbodiimide was added and the mixture was stirred for 1 h. 43 mg of (1H-Tetrazol-5-ylmethyl)amine dihydrochloride was added followed by 1 mL triethylamine. The mixture was stirred for 18 h, filtered through celite, and the solvents removed by evaporation. The resulting residue was purified by reverse phase H.P.L.C. to give the title compound as a white solid; 18 mg.

Workup

  1. stirringThe mixture was stirred for 18 h
  2. filtrationfiltered through celite
  3. customthe solvents removed by evaporation
  4. customThe resulting residue was purified by reverse phase H.P.L.C

Sources & evidence

ORD record
ord-493b0c91ae4e4c64ab30d1e22e49d8f6
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

Loading…