tert-Butanol → 3-azido-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-propanoic acid, ethyl ester

HRID 1327

Reaction equation

HRID 1327 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:15])=[N+:2]=[N-:3].[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH2:18].C(O)(C)(C)C.[K]>O1CCCC1.C(O)(C)(C)C.O1CCCC1>[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH2:18][CH2:17][C:16]([O:20][CH2:21][CH3:22])=[O:19])[C:5]1=[O:15])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8821Ethyl AcrylateHCID 5462222PotassiumHCID 109325203-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 867497903-azido-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-propanoic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 66775918Tert-butanol tetrahydrofuranSolvent

Procedure

A solution of 3-azido-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one [prepared as described by Watthey et al., J. Med. Chem., 28, p. 1511-15156 (1985)] in tetrahydrofuran/tert-butanol was cooled to 0° C. and treated with ethyl acrylate and 1N tert-butanol, potassium salt/tetrahydrofuran according to the procedure of Example 40 part (a) affording 3-azido-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-propanoic acid, ethyl ester as a syrup. TLC (ethyl ether:hexane, 1:1) Rf =0.45.

Sources & evidence

ORD record
ord-75d6830239304b61acc836550d1f3a66
Source dataset
uspto-grants-1998_03
Patent number
US05723602

Linked notes

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