4-Methylmorpholine → HCID 22878776, compound

HRID 2292888Notes

Reaction equation

HRID 2292888 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]([CH3:20])=[CH:16][CH:15]=2)[C:3]1=[O:21].[CH2:22]([O:24][C:25](=[O:48])[C@H:26](OS(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH2:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH3:23].CN1CCOCC1>C(OCC)(=O)C.CCCCCC>[CH2:22]([O:24][C:25]([C@@H:26]([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:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[C:3]1=[O:21])[CH2:27][CH2:28][CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)=[O:48])[CH3:23]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 21478497HCID 21478497, compoundHCID 54177175HCID 54177175, compound

Product 1

HCID 22878776HCID 22878776, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The reaction of 5.4 g of 3-amino-1-(p-methylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one with 8.84 g of (R)-alpha-[[(4-nitrophenyl)sulfonyl]oxy]-4-cyclohexylbutyric acid ethyl ester and 2.6 ml of N-methylmorpholine yields the two diastereoisomeric esters 3-(S)-[(1-(S)-ethoxycarbonyl-3-cyclohexyl-propyl)-amino]-1-(p-methylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one and 3-(R)-[(1-(S)-ethoxycarbonyl-3-cyclohexyl-propyl)-amino]-1-(p-methylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one, Rf values (eluant ethyl acetate/hexane 1:2) non-polar component 0.58, polar component 0.39.

Sources & evidence

ORD record
ord-412c8cd4468b484d95380c9159fadc2b
Source dataset
uspto-grants-1997_11
Patent number
US05683997

Reaction notes

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