Bromoacetyl bromide → (3aR*,10aS*)-4-(Bromoacetyl)-9-(4-nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one

HRID 356194Notes

Reaction equation

HRID 356194 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[C@H:14]3[CH2:17][CH2:18][CH2:19][C@H:13]3[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:26][CH2:27][C:28](Br)=[O:29]>C(OCC)(=O)C.CCCCCC>[Br:26][CH2:27][C:28]([N:12]1[C@@H:13]2[CH2:19][CH2:18][CH2:17][C@@H:14]2[C:15](=[O:16])[N:9]([CH2:8][C:7]2[CH:24]=[CH:25][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:10]2[CH:23]=[CH:22][CH:21]=[CH:20][C:11]1=2)=[O:29]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 54563031(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 70110396(3aR*,10aS*)-4-(Bromoacetyl)-9-(4-nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-oneYield 37%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using (3aR*,10aS*)-9-(4-nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one and bromoacetyl bromide, the titled compound was synthesized in substantially the same manner as in Working Example 185 in a yield of 37%, m.p. 160.5°-161.5° C. (ethyl acetate-hexane).

Sources & evidence

ORD record
ord-0d21f1acec9842dea40c3d33d999461b
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

Loading…