Trifluoroacetic acid → HCID 68745182, compound

HRID 2093607Notes

Reaction equation

HRID 2093607 reaction equation
O1C2C=CC=CC=2N=C1.C(OC([N:17]1[CH2:22][CH2:21][CH2:20][C@H:19]([CH2:23][NH:24][C:25](=[O:46])[C:26]2[CH:31]=[CH:30][C:29]([C:32]3[O:33][C:34]4[C:40]([CH:41]([CH3:43])[CH3:42])=[CH:39][C:38]([C:44]#[N:45])=[CH:37][C:35]=4[N:36]=3)=[CH:28][CH:27]=2)[CH2:18]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:44]([C:38]1[CH:39]=[C:40]([CH:41]([CH3:43])[CH3:42])[C:34]2[O:33][C:32]([C:29]3[CH:28]=[CH:27][C:26]([C:25]([NH:24][CH2:23][C@H:19]4[CH2:20][CH2:21][CH2:22][NH:17][CH2:18]4)=[O:46])=[CH:31][CH:30]=3)=[N:36][C:35]=2[CH:37]=1)#[N:45]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86647805HCID 86647805, compound

Product 1

HCID 68745182HCID 68745182, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl(3R)-3-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)piperidine-1-carboxylate benzoxazole (201 mg, EXAMPLE 94) in 15 ml dichloromethane was added trifluoroacetic acid (5 ml). The mixture was stirred at room temperature for 30 min. The mixture was concentrated in vacuo, diluted with 40 ml of ethyl acetate, and basified by slow and cautious addition of 40 ml of saturated aqueous sodium carbonate. The phases were separated and the aqueous phase was extracted with 40 ml of ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title compound (144 mg, 89%). Mass spectrum (ESI) 403.3 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with 40 ml of ethyl acetate
  3. additioncautious addition of 40 ml of saturated aqueous sodium carbonate
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with 40 ml of ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e97af8d752b462c93286e669fe5ca6b
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

Loading…