4-Methylmorpholine → HCID 22878777, compound

HRID 2292886Notes

Reaction equation

[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:3]1=[O:23].[CH2:24]([O:26][C:27](=[O:50])[C@H:28](OS(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH2:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH3:25].CN1CCOCC1>>[CH2:24]([O:26][C:27]([C@@H:28]([NH:1][C@@H:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:3]1=[O:23])[CH2:29][CH2:30][CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)=[O:50])[CH3:25]

Participants

Reactant 3

HCID 79724-Methylmorpholine

HCID 21478481HCID 21478481, compound

HCID 54177175HCID 54177175, compound

Product 1

HCID 22878777HCID 22878777, compound

Procedure

The reaction of 15 g of 3-amino-1-(p-nitrobenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one with 22.1 g of (R)-alpha-[[(4-nitrophenyl)sulfonyl]oxy]-4-cyclohexylbutyric acid ethyl ester and 6.45 ml N-methylmorpholine yields the two diastereoisomeric esters 3-(S)-[(1-(S)-ethoxycarbonyl-3-cyclohexyl-propyl)-amino]-1-(p-nitrobenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one and 3-(R)-[(1-(S)-ethoxycarbonyl-3-cyclohexyl-propyl)-amino]-1-(p-nitrobenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one. Rf values (eluant ethyl acetate/hexane 1:2) non-polar component 0.78, polar component 0.69.

Sources & evidence

ORD record: ord-bea7108f996f4250a202ba9be241ba63
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05683997

Reaction notes

Loading…