Trifluoroacetic acid → HCID 67115886, compound

HRID 77376Notes

Reaction equation

HRID 77376 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:25]=[CH:24][C:23]([N:26]2[CH:32]3[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]3)[CH2:28][CH2:27]2)=[CH:22][C:10]=1[C:11]([NH:13][CH2:14][C:15]([O:17][C:18](C)(C)C)=[O:16])=[O:12]>ClCCl.CO>[NH2:8][C:9]1[CH:25]=[CH:24][C:23]([N:26]2[CH:32]3[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]3)[CH2:28][CH2:27]2)=[CH:22][C:10]=1[C:11]([NH:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67416661Tert-butyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate2×

Product 1

HCID 67115886HCID 67115886, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (3.26 g, 28.0 mmol) was added to a solution of tert-butyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate (Intermediate 7B) (1.0 g, 2.67 mmol) in dichloromethane (20 mL) and methanol (2 mL). The resulting solution was stirred for 7 hours before leaving to stand over the weekend. The resultant crude material purified using a 5 g SCX cartridge to afford methyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate. This was dissolved in tetrahydrofuran (20 mL) and 1M lithium hydroxide solution (5.34 mL, 5.34 mmol) and water (2 mL) was added and the solution stirred overnight. The reaction mixture was then acidified and purified using a 5 g SCX cartridge to afford 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetic acid (849 mg, 2.67 mmol).

Workup

  1. custombefore leaving
  2. customThe resultant crude material purified

Sources & evidence

ORD record
ord-bc7115af85f94872b7b4c5ddb2c86738
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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