Dimethylformamide → HCID 70091673, compound

HRID 1728386Notes

Reaction equation

CC(C)(O[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])C.C(N([CH:41]([CH3:43])[CH3:42])CC)(C)C.[NH2:44][CH2:45][C:46]1[CH:54]=[CH:53][C:49]([C:50]([OH:52])=[O:51])=[CH:48][CH:47]=1.[CH3:55]N(C=O)C>>[CH3:42][C:41]([C:5]([C@H:7]([NH:25][C@@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:31]([NH:44][CH2:45][C:46]1[CH:47]=[CH:48][C:49]([C:50]([OH:52])=[O:51])=[CH:53][CH:54]=1)=[O:33])[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])=[O:6])([CH3:43])[CH3:55]

Participants

Reactant 4

HCID 6228Dimethylformamide2×

HCID 655264-(Aminomethyl)Benzoic Acid

HCID 81531Diisopropylethylamine

HCID 54449037HCID 54449037, compound

Product 1

HCID 70091673HCID 70091673, compound

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 a mixture of 0.174 mL of diisopropylethylamine, 1 mL DMF, and 1.1 mL of 0.45M hydroxybenzotriazol-benzotriazoltetramethyluronium hexafluorophosphate in DMF at 5° C. 75 mg of 4-(Aminomethyl)-benzoic acid was added and the mixture was stirred for 24 h. The solvents were removed by evaporation to give the title compound; 84 mg.

Workup

customThe solvents were removed by evaporation

Sources & evidence

ORD record: ord-9d583ee1701e41388ee2eb967967611f
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326760

Reaction notes

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