4-Methylmorpholine → HCID 22878778, compound

HRID 2292887Notes

Reaction equation

HRID 2292887 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]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[C:3]1=[O:24].[CH2:25]([O:27][C:28](=[O:51])[C@H:29](OS(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH2:30][CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[CH3:26].CN1CCOCC1>C(OCC)(=O)C.CCCCCC>[CH2:25]([O:27][C:28]([C@@H:29]([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]([C:20]([CH3:21])([CH3:23])[CH3:22])=[CH:18][CH:19]=2)[C:3]1=[O:24])[CH2:30][CH2:31][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)=[O:51])[CH3:26]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 21478488HCID 21478488, compoundHCID 54177175HCID 54177175, compound

Product 1

HCID 22878778HCID 22878778, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The reaction of 3.55 g of 3-amino-1-(p-tert-butylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one with 2.5 g of (R)-alpha-[[(4-nitrophenyl)sulfonyl]oxy]-4-cyclohexylbutyric acid ethyl ester and 1.03 ml of N-methylmorpholine yields the two diastereoisomeric esters 3-(S)-[(1-(S)-ethoxycarbonyl-3-cyclohexyl-propyl)-amino]-1-(p-tert-butylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one and 3-(R)-[(1-(S)-ethoxycarbonyl-3-cyclohexyl-propyl)-amino]-1-(p-tert-butylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one, Rf values (eluant ethyl acetate/hexane 1:2) non-polar component 0.42, polar component 0.26.

Sources & evidence

ORD record
ord-9ec31d5dcb5847849bfed04596b2055e
Source dataset
uspto-grants-1997_11
Patent number
US05683997

Reaction notes

Loading…