Ethyl Acetate → 3(S)-benzyloxycarbonylamino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one

HRID 464832Notes

Reaction equation

HRID 464832 reaction equation
C(OCC)(=O)C.Cl.[NH2:8][C@@H:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:10]1.[CH2:21]([O:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH2:21]([O:28][C:29]([NH:8][C@@H:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:10]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 18599716(S)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochloride

Product 1

HCID 185997183(S)-benzyloxycarbonylamino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 100 ml of ethyl acetate and 50 ml of water is added 1.5 g of 3(S)-amino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one hydrochloride, and 1.5 ml of benzyloxycarbonyl chloride is added dropwise to the mixture at ice bath temperature with stirring. After stirring for 1 hour, the ethyl acetate layer separated, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue is added ethyl ether and the deposited crystals are collected by filtration to give 2 g of 3(S)-benzyloxycarbonylamino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one. This product is recrystallized from a mixture of ethyl acetate and ether to give colorless needles melting at 157°-159° C.

Workup

  1. additionis added dropwise to the mixture at ice bath temperature
  2. stirringAfter stirring for 1 hour
  3. customthe ethyl acetate layer separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue is added ethyl ether
  8. filtrationthe deposited crystals are collected by filtration

Sources & evidence

ORD record
ord-fca722504f4b4932953bfe89579ccffe
Source dataset
uspto-grants-1985_10
Patent number
US04548932

Reaction notes

Loading…