Dicyclohexylcarbodiimide → HCID 10370529, compound

HRID 1728382Notes

Reaction equation

HRID 1728382 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=NNC=2C=CC=1.[N:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][NH2:52])[CH:46]=1.C1(N=C=NC2CCCCC2)CCCCC1>O.CN(C=O)C>[CH3:1][C:2]([O:4][C:5](=[O:6])[C@H:7]([NH:25][C@H:26]([C:31]([NH:52][CH2:51][C:47]1[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=1)=[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])([CH3:34])[CH3:3]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 310183-PyridinemethanamineHCID 54449037HCID 54449037, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 10370529HCID 10370529, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

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 2.5 mL of DMF. 39.2 mg of hydroxybenzotriazol.H2O was added to the mixture followed by 0.026 mL of (pyridin-3-ylmethyl)amine. The mixture was cooled to 0° C. and 52.8 mg dicyclohexylcarbodiimide was added. The mixture was warmed to 23° C. and stirred for 24 h. The solvents were removed by evaporation and the resultant residue was diluted with ethyl acetate. The mixture was extracted with a saturated solution of sodium bicarbonate and the organic layer was separated, dried (MgSO4), and filtered. The solvent was removed by evaporation to afford the title compound; 139 mg.

Workup

  1. temperatureThe mixture was warmed to 23° C.
  2. customThe solvents were removed by evaporation
  3. additionthe resultant residue was diluted with ethyl acetate
  4. extractionThe mixture was extracted with a saturated solution of sodium bicarbonate
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ea08da99fbfa42fbb81fc4f9017edad1
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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