Methanol → HCID 13749515, compound

HRID 2118873Notes

Reaction equation

HRID 2118873 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH:16]([C:18](C)=[O:19])[CH3:17])[C:10]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[OH:23].[OH-].[Na+]>O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH:16]([C:18]([OH:19])=[O:23])[CH3:17])[C:10]1=[O:21])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53707838HCID 53707838, compound

Product 1

HCID 13749515HCID 13749515, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve 2.59 g 3-(S)-t-butoxycarbonylamino-1-(1-methylcarbonylethyl)perhydroazepin-2-one in 10 ml. methanol and 10 ml water and add 0.5 ml 50% NaOH solution. Store the mixture at room temperature for 2 hours and then concentrate at aspirator pressure to a syrup. Dissolve the syrup in water and chill the solution in an ice bath. Add 6N hydrochloric acid to pH 2 then extract the solution several times with ethyl acetate. Dry the combined extracts over MgSO4, filter and concentrate the filtrate at aspirator pressure and isolate 3-(S)-t-butoxycarbonylamino-1-(1-carboxyethyl)perhydroazepin-2-one as an oil (2.04 g) which is a mixture of diastereomers. Separate the isomers on a column of XAD2 resin at 50° C. using 0.1N NH4OH containing 6% acetonitrile as eluent. Isolate the ammonium salt of the desired isomer as the one which elutes first (u.v. and refractive index detection).

Workup

  1. concentrationconcentrate at aspirator pressure to a syrup
  2. dissolutionDissolve the syrup in water
  3. temperaturechill the solution in an ice bath
  4. additionAdd 6N hydrochloric acid to pH 2
  5. extractionthen extract the solution several times with ethyl acetate
  6. dry with materialDry the combined extracts over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate the filtrate at aspirator pressure

Sources & evidence

ORD record
ord-b2376ec042074e53a211f96ddf49780b
Source dataset
uspto-grants-1987_07
Patent number
US04680392

Reaction notes

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