Hydrochloric Acid → HCID 67716932, compound

HRID 2292884Notes

Reaction equation

HRID 2292884 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]([CH:20]([CH3:22])[CH3:21])=[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.Cl>C(OCC)(=O)C.C(OCC)(=O)C.O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:24]([O:26][C:27]([C@@H:28]([NH: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:15]=[CH:16][C:17]([CH:20]([CH3:21])[CH3:22])=[CH:18][CH:19]=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

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 79724-MethylmorpholineHCID 21478504HCID 21478504, compoundHCID 54177175HCID 54177175, compound

Product 1

HCID 67716932HCID 67716932, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
75 °C

Procedure

1.5 g of 3-(R/S)-amino-1-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one and 2.23 g of (R)-alpha-[[(4-nitrophenyl)-sulfonyl]oxy]-4-cyclohexylbutyric acid ethyl ester (Helv. Chim. Acta 71 (2), 337, 1988) are combined and, at 40° C., 0.67 ml of N-methylmorpholine is added. The mixture is heated at 75° C. for 15 h, cooled, diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and water and finally with dilute hydrochloric acid and brine. Flash chromatography (80 g of silica gel, eluant ethyl acetate/hexane 1:2) yields the two diastereoisomers which, after being dissolved in ethyl acetate/tetrahydrofuran, were each converted separately into the corresponding hydrochloride with 3 equivalents of 1N hydrochloric acid. Rf values of the free bases (eluant: ethyl acetate/hexane 1:2):

Workup

  1. customare combined and, at 40° C.
  2. temperaturecooled
  3. washwashed with aqueous sodium hydrogen carbonate solution and water and finally with dilute hydrochloric acid and brine
  4. customFlash chromatography (80 g of silica gel, eluant ethyl acetate/hexane 1:2) yields the two diastereoisomers which

Sources & evidence

ORD record
ord-73a3921dbcdd4c45afa3d1ebb022cb5b
Source dataset
uspto-grants-1997_11
Patent number
US05683997

Reaction notes

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