Hydrochloric Acid → HCID 18605784, compound

HRID 1249273Notes

Reaction equation

HRID 1249273 reaction equation
[C:1]([CH:4]([N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]([NH:13][CH:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]1=[O:28])[CH3:5])([OH:3])=[O:2].Cl.[CH2:30](O)[CH3:31]>>[CH2:30]([O:2][C:1]([CH:4]([N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]([NH:13][CH:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]1=[O:28])[CH3:5])=[O:3])[CH3:31]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13749509HCID 13749509, compound

Product 1

HCID 18605784HCID 18605784, compound

Procedure

A solution of 1-(1-carboxyethyl)-3-(S)-[(1-ethoxycarbonyl-3-phenylpropyl)amino]perhydroazepin-2-one (2.94 g.), a diastereoisomeric mixture prepared as in Example 13 from Isomer A of Example 12, with 40 ml. of ethanol was cooled to 0° and saturated with hydrogen chloride. After standing overnight at room temperature the solution was concentrated under vacuum. Dissolution in water, adjustment to pH 7, extraction with ether and concentration gave product as a colorless oil, weight 2.87 g. Tlc on silica gel indicated the presence of two diastereomers. If desired, the isomers may be separated by chromatography on silica gel and elution with hexane-ethyl acetate.

Workup

  1. concentrationthe solution was concentrated under vacuum
  2. dissolutionDissolution in water
  3. extractionadjustment to pH 7, extraction
  4. concentrationwith ether and concentration
  5. customgave product as a colorless oil, weight 2.87 g
  6. customthe isomers may be separated by chromatography on silica gel and elution with hexane-ethyl acetate

Sources & evidence

ORD record
ord-bbe87c56ae5343cc9f99bdb6af0fd997
Source dataset
uspto-grants-1986_12
Patent number
US04629787

Reaction notes

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