Ammonia → HCID 13985439, compound

HRID 1979523Notes

Reaction equation

HRID 1979523 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[C:14](=O)[O:13]C1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:22]>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@@H:15]([CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[C:14]([NH2:22])=[O:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13985433Benzyl (4S)-5-oxo-4-(3-oxobutyl)-1,3-oxazolidine-3-carboxylate

Product 1

HCID 13985439HCID 13985439, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ten grams of the (S)-3-(benzyloxycarbonyl)-4-(3-oxobutyl)-5-oxazolidinone from Example 4 is dissolved in 480 ml of distilled tetrahydrofuran, followed by 160 ml of ammonia at 0° C. The reaction mixture is stirred at 0° for 5 hours, then at ambient temperature overnight. After stripping under vacuum to dryness, the reaction mixture yields a white solid which is recrystallized from hot ethyl acetate to give 8.8 g of (S)-2-(benzyloxycarbonylamino)-5-oxo-hexanamide as a white solid (82% yield), mp 142°-144°;

Workup

  1. customat ambient temperature
  2. customovernight
  3. customthe reaction mixture yields a white solid which
  4. customis recrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-d531600b7e73466e8543d974332dfdd6
Source dataset
uspto-grants-1984_11
Patent number
US04481190

Reaction notes

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