Ethyl bromoacetate → benzyl 3(S)-ethoxycarbonylmethylamino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate

HRID 280930

Reaction equation

HRID 280930 reaction equation
Cl.[NH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[O:5][CH2:4]1.C(N(CC)CC)C.Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>C(O)C>[CH2:38]([O:37][C:35]([CH2:34][NH:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[O:5][CH2:4]1)=[O:36])[CH3:39]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 18599732benzyl 3(S)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate hydrochloride

Product 1

HCID 54078584benzyl 3(S)-ethoxycarbonylmethylamino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetateYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol is dissolved 0.5 g of benzyl 3(S)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate hydrochloride obtained in Example 5, and triethylamine (0.49 g) and ethyl bromoacetate (0.46 g) are added to the solution. After the solution is stirred for 4 days, the solution is dried under reduced pressure. The residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:3) to give 0.28 g of benzyl 3(S)-ethoxycarbonylmethylamino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate as a pale yellow oil.

Workup

  1. additionare added to the solution
  2. customthe solution is dried under reduced pressure
  3. customThe residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:3)

Sources & evidence

ORD record
ord-66824191942741da8514a1def9f6f374
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Linked notes

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