Dimethylformamide → HCID 70091779, compound

HRID 1728380Notes

Reaction equation

HRID 1728380 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].O[N:36]1[C:40](=O)CCC1=O.[CH2:43]([N:45](CC)CC)C.C[N:51]([CH:53]=O)[CH3:52]>>[CH3:1][C:2]([O:4][C:5](=[O:6])[C@H:7]([NH:25][C@H:26]([C:31]([NH:45][CH2:43][C:52]1[NH:51][CH:53]=[CH:40][N:36]=1)=[O:33])[CH2:27][CH:28]([CH3:30])[CH3:29])[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])([CH3:3])[CH3:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 54449037HCID 54449037, compound

Product 1

HCID 70091779HCID 70091779, compound

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 40 mg N-hydroxysuccinimide in 5 mL DMF. To the mixture was added 27 mg of (1H-Imidazo-2-ylmeth yl)amine followed by 1 mL triethylamine. The mixture was stirred for 18 h, filtered through celite, and the solvents were removed by evaporation. The resulting residue was purified by reverse phase H.P.L.C. to afford the title compound as a white solid; 44 mg.

Workup

  1. filtrationfiltered through celite
  2. customthe solvents were removed by evaporation
  3. customThe resulting residue was purified by reverse phase H.P.L.C

Sources & evidence

ORD record
ord-119a147599a143838f5c6e90ec4bc19b
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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