Trifluoroacetic acid → HCID 52945520, compound

HRID 249885Notes

Reaction equation

HRID 249885 reaction equation
[N:1]12[CH2:8][CH:7]([NH:9][C:10]([C:12]3[C:17]4[N:18]=[C:19]([NH:21]C(=O)OC(C)(C)C)[O:20][C:16]=4[CH:15]=[CH:14][CH:13]=3)=[O:11])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]12[CH2:8][C@@H:7]([NH:9][C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[O:20][C:19]([NH2:21])=[N:18][C:17]=34)=[O:11])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66873971HCID 66873971, compound

Product 1

HCID 52945520HCID 52945520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(quinuclidine-8-yl-carbamoyl)benzoxazole-2-yl-carbamate (0.210 g, 0.54 mmol), in CH2Cl2 (5 mL) was added TFA(2 mL) and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was concentrated and the crude material was treated with aqueous NaHCO3 to adjust the pH to 7 and then extracted with CH2Cl2 (5×50 mL). The combined organic phase was concentrated and purified by preparative TLC (90:9:1 CH2Cl2/CH3OH/concentrated NH4OH) to afford (S)—N-(quinuclidine-8-yl)-2-aminobenzoxazole-4-carboxamide which was converted to the hydrochloride salt following general procedure GP-D1. 1H NMR and MS consistent.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe crude material was treated with aqueous NaHCO3
  3. extractionextracted with CH2Cl2 (5×50 mL)
  4. concentrationThe combined organic phase was concentrated
  5. custompurified by preparative TLC (90:9:1 CH2Cl2/CH3OH/concentrated NH4OH)

Sources & evidence

ORD record
ord-564ac152bbe84bf18d97dfc2dac47698
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

Loading…