tert-Butyl [3-(cyclopropylmethyl)-2-oxo-1,3-diazepan-1-yl]acetate → [3-(Cyclopropylmethyl)-2-oxo-1,3-diazepan-1-yl]acetic acid

HRID 1442872Notes

Reaction equation

HRID 1442872 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[C:6]2=[O:20])[CH2:3][CH2:2]1>C(Cl)Cl.C(C(O)=O)(F)(F)F>[CH:1]1([CH2:4][N:5]2[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:12][C:13]([OH:15])=[O:14])[C:6]2=[O:20])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86606171tert-Butyl [3-(cyclopropylmethyl)-2-oxo-1,3-diazepan-1-yl]acetate

Product 1

HCID 18442648[3-(Cyclopropylmethyl)-2-oxo-1,3-diazepan-1-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl [3-(cyclopropylmethyl)-2-oxo-1,3-diazepan-1-yl]acetate from Step D (240 mg, 0.85 mmol) in CH2Cl2 (5 mL) and CF3CO2H (2 mL) was stirred at ambient temperature for 3 h. The mixture was concentrated in vacuo and the residue was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=227 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by HPLC
  3. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-6f862e5645b84c52b553ff28cd0d0c83
Source dataset
uspto-grants-2010_02
Patent number
US07659300B2

Reaction notes

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