Dimethylformamide → HCID 18653525, compound

HRID 1728383Notes

Reaction equation

HRID 1728383 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].C[N:36]([CH:38]=O)C.OC1C2[N:48]=[N:47][NH:46]C=2C=CC=1.[CH:50]1([N:56]=C=NC2CCCCC2)CCCCC1>O>[CH3:3][C:2]([O:4][C:5](=[O:6])[C@H:7]([NH:25][C@H:26]([C:31]([NH:56][CH2:50][C:38]1[N:36]=[N:48][NH:47][N:46]=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

6

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 54449037HCID 54449037, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 18653525HCID 18653525, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 mL DMF. 39.2 mg of hydroxybenzotriazol.H2O was added to the mixture, followed by 28.2 mL of N-methyl-4-morpholine and 38.3 mg of (2-methyl-2H-tetrazo-5-ylmethyl)amine The mixture was cooled to 0° C. and 52.8 mg of dicyclohexylcarbodiimide was added. The mixture was allowed to warm to 23° C. and was 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; 120 mg.

Workup

  1. temperatureto warm 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-ea5c4895f617448b854ddba883134008
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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