Triethylamine → 4-Cyclobutanecarbonyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 1944109Notes

Reaction equation

HRID 1944109 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][CH2:26][N:25]([C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[O:6])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 581477184-Cyclobutanecarbonyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclobutanecarbonyl chloride (3.7 ml) and triethylamine (14 ml) were added to a solution of [1,4]diazepane-1-carboxylic acid tert-butyl ester (4.9 ml) in dichloromethane (175 ml). After stirring for 1 h at room temperature, the reaction mixture was washed with water, an aqueous HCl solution (1 N), water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a493c1ac19ca4f53bc729ea0e24661d6
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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