Hydrochloric Acid → HCID 67716932, compound

HRID 2292885Notes

Reaction equation

HRID 2292885 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][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:25].C(OCC)(=O)C.CCCCCC.Cl>C(OCC)(=O)C.O1CCCC1>[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

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11280833109010-59-5HCID 21226206Ethyl acetate hexane2×HCID 21478504HCID 21478504, compound

Product 1

HCID 67716932HCID 67716932, compound

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

Was prepared analogously to Example 1c) starting from 3-(R/S)-amino-1-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-benzazepin-2-one and (R)-alpha-[[(4-nitrophenyl)sulfonyl]-oxy]-4-phenylbutyric acid ethyl ester (Helv. Chim. Acta 71 (2), 337, 1988). Flash chromatography (eluant: ethyl acetate/hexane: 1:4) yields the two pure diastereoisomeric forms which, after being dissolved in ethyl acetate/tetrahydrofuran, are each converted separately into the corresponding hydrochloride by treatment with 3 equivalents of 1N hydrochloric acid. Rf values of the free bases (eluant ethyl acetate/hexane):

Workup

  1. customWas prepared analogously to Example 1c)

Sources & evidence

ORD record
ord-6eddc9e658e84a58ba251bb53a143841
Source dataset
uspto-grants-1997_11
Patent number
US05683997

Reaction notes

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