Trifluoroacetic acid → 3-Amino-oxetane-3-carboxylic acid (1-pyridin-2-yl-cyclopropyl)-amide formate

HRID 1040555Notes

Reaction equation

HRID 1040555 reaction equation
C([O:5][C:6](=[O:24])[NH:7][C:8]1([C:12](=[O:23])[NH:13][C:14]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:16][CH2:15]2)[CH2:11][O:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:6]([OH:24])=[O:5].[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1([NH:13][C:12]([C:8]2([NH2:7])[CH2:11][O:10][CH2:9]2)=[O:23])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58430978[3-(1-Pyridin-2-yl-cyclopropylcarbamoyl)-oxetan-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 673912253-Amino-oxetane-3-carboxylic acid (1-pyridin-2-yl-cyclopropyl)-amide formateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(1-pyridin-2-yl-cyclopropylcarbamoyl)-oxetan-3-yl]-carbamic acid tert-butyl ester (100 mg, 0.30 mmol) in CH2Cl2 (2 mL) was added TFA (1 mL). The solution was stirred at room temperature for 17 h and then concentrated in vacuo. The residue was purified by reverse phase HPLC to give 3-amino-oxetane-3-carboxylic acid (1-pyridin-2-yl-cyclopropyl)-amide formate as a white powder (72 mg, 86%) after lyophilization, m/z 234 (free base) [M+1]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-668b414fdd1043419b3eaa57473c49da
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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