Hydrochloric Acid → HCID 67785996, compound

HRID 1723340Notes

Reaction equation

HRID 1723340 reaction equation
C(OC([N:8]1[CH2:14][C@@:13]([C:22](=[O:24])[NH2:23])([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:12]2[CH:25]=[C:26]([CH2:32][CH3:33])[C:27]([CH2:30][CH3:31])=[C:28]([Cl:29])[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[ClH:29].[Cl:29][C:28]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:14][C@@:13]([C:22](=[O:24])[NH2:23])([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)[C:12]=2[CH:25]=[C:26]([CH2:32][CH3:33])[C:27]=1[CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131716047HCID 131716047, compound

Product 1

HCID 67785996HCID 67785996, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 14.3 g(0.03 moles) of (R)-3-t-butyloxycarbonyl-6-chloro-7,8-diethylcarbamyl-1-(4'-hydroxyphenyl) 2,3,4,5-tetrahydro-1H-3-benzazepine, in 100 ml of ethyl acetate at 25° C. was treated with 50 ml of ethereal hydrogen chloride under argon atmosphere. After stirring for 72 hours, the reaction mixture was concentrated under reduced pressure and chased with 200 ml. of dry toluene. The resulting residue was triturated with 00 ml of ethyl acetate to give (R)-6-chloro-7,8-diethycarbamoyl-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H 3-benzazepine hydrochloride, M.P. 185°-190° C. The Rf and the NMR of this compound was similar to that of the corresponding racemic compound of Example 5.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure and chased with 200 ml
  2. customThe resulting residue was triturated with 00 ml of ethyl acetate

Sources & evidence

ORD record
ord-2d56670025434587807a1d98c9dd0628
Source dataset
uspto-grants-1989_08
Patent number
US04861771

Reaction notes

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