Trifluoroacetic acid → HCID 71145730, compound

HRID 535315Notes

Reaction equation

HRID 535315 reaction equation
C(OC([N:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[C:28](=[O:29])[CH2:27][C:26]4[C:21](=[CH:22][C:23]([O:32][CH:33]([CH3:35])[CH3:34])=[C:24]([O:30][CH3:31])[CH:25]=4)[C@@H:20]3[C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)=[CH:15][CH:14]=2)([OH:12])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([C@H:20]2[C:21]3[C:26](=[CH:25][C:24]([O:30][CH3:31])=[C:23]([O:32][CH:33]([CH3:34])[CH3:35])[CH:22]=3)[CH2:27][C:28](=[O:29])[N:19]2[C:16]2[CH:17]=[CH:18][C:13]([C:10]3([OH:12])[CH2:11][NH:8][CH2:9]3)=[CH:14][CH:15]=2)=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71145832HCID 71145832, compound

Product 1

HCID 71145730HCID 71145730, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 56 was obtained from example 55. A solution of 3-{4-[(S)-1-(4-Chloro-phenyl)-7-isopropoxy-6-methoxy-3-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-phenyl}-3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (70 mg, 0.118 mmol) in DCM (1 ml) was immersed in an ice-bath followed by addition of TFA (0.045 ml, 0.590 mmol). The yellow reaction solution turned brown and was stirred for 30 minutes. The reaction mixture was treated with ice/saturated aq. sodium hydrogencarbonate solution and extracted with DCM. The organic phase was separated, dried over sodium sulfate, filtered and concentrated in vacuo to obtain the title compound as yellowish solid.

Workup

  1. customExample 56 was obtained from example 55
  2. additionThe reaction mixture was treated with ice/saturated aq. sodium hydrogencarbonate solution
  3. extractionextracted with DCM
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9d5cbe67fa547c38101e5fdcf0cf43f
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

Loading…