Trifluoroacetic acid → HCID 58674938, compound

HRID 2244415Notes

Reaction equation

HRID 2244415 reaction equation
C(OC([NH:8][C:9]1[N:14]=[C:13]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH:12]=[CH:11][CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:8][C:9]1[N:14]=[C:13]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 58674936HCID 58674936, compound

Product 1

HCID 58674938HCID 58674938, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acetic acid 6-tert-butoxycarbonylamino-pyridin-2-ylmethyl ester (0.85 g, 3.18 mmol) in dichloromethane (30.00 ml) was cooled to 0° C. and trifluoroacetic acid (2.40 ml) was added dropwise. After stirring at room temperature for 3 h, further trifluoroacetic acid (1.50 ml) was added and stirring was maintained for further 2 h. The reaction mixture was basified with 1 N sodium bicarbonate (54.00 ml) to a pH 8. The organic phase was separated and the aqueous phase extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate and evaporated to yield pure acetic acid 6-amino-pyridin-2-ylmethyl ester (0.54 g, 100%) as a white solid, MS (ISP): m/e=167.4 (M+H+).

Workup

  1. stirringstirring
  2. temperaturewas maintained for further 2 h
  3. customThe organic phase was separated
  4. extractionthe aqueous phase extracted twice with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-6777902dc51947a28fc2c1cb3c6cba4d
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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