L-Pyroglutamic Acid → trans-3-(2-indolecarboxamido)-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamide

HRID 345162Notes

Reaction equation

HRID 345162 reaction equation
[NH2:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([NH2:22])=[O:21])[C:3]1=[O:23].[NH:24]1[C:28](=O)[CH2:27][CH2:26][C@H:25]1[C:30]([OH:32])=O>CN(C)C=O>[NH:24]1[C:28]2[C:27](=[CH:3][CH:2]=[CH:8][CH:7]=2)[CH:26]=[C:25]1[C:30]([NH:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([NH2:22])=[O:21])[C:3]1=[O:23])=[O:32]

Participants

4

Reactant 2

HCID 7405L-Pyroglutamic AcidHCID 67931351trans-3-amino-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamide

Product 1

HCID 69609074trans-3-(2-indolecarboxamido)-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of dimethylformamide are dissolved 1.00 g of trans-3-amino-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamide as obtained in (ii) of Example 30 and 0.42 g of L-pyroglutamic acid, and the same reaction and treatment as in Example 3 is carried out to give A isomer (0.41 g) and B isomer (0.42 g) of trans-2-oxo-3-[5-oxo-2(S)-pyrrolidinecarboxamido]-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamide.

Sources & evidence

ORD record
ord-891738459dc14abcb7fee20c5530e459
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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