4-(4,4-Dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester → 5-Oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 10182Notes

Reaction equation

HRID 10182 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][CH:19](OC)[O:20]C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][CH:19]=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 692244834-(4,4-Dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 113121495-Oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 32.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(4,4-dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3 g, 9.08 mmole) in glacial acetic acid containing 0.5 mL water (10 mL) was stirred at room temperature for 24 hours. The solution was concentrated at 35° C. under reduced pressure, and the residue was partitioned between saturated aqueous sodium bicarbonate and diethyl ether. The organic phase was dried (magnesium sulfate), concentrated, and the residue recrystallized from diethyl ether/hexane to give 5-oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.85 g,), m.p. 86–87° C.

Workup

  1. concentrationThe solution was concentrated at 35° C. under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate and diethyl ether
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customthe residue recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-ce360d8cda6442bfbb83adcdd193eb04
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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