Trifluoroacetic acid → HCID 72303899, compound

HRID 1747083Notes

Reaction equation

HRID 1747083 reaction equation
C(OC1C=CC(C[O:11][NH:12][C:13]([CH:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[N:17]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]3[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:16]2[C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=2[Cl:44])=[O:14])=CC=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:44][C:38]1[CH:39]=[C:40]([Cl:43])[CH:41]=[CH:42][C:37]=1[CH:16]1[CH:15]([C:13]([NH:12][OH:11])=[O:14])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[N:17]1[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[NH:32][S:33]([CH3:36])(=[O:34])=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72303814HCID 72303814, compound

Product 1

HCID 72303899HCID 72303899, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 644 mg of (3RS,4RS)—N-[(4-tert-butoxybenzyl)oxy]-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(mesyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide in 8.4 ml of dichloromethane was added 0.94 ml of trifluoroacetic acid under ice-cooling, followed by stirring at room temperature for 1 hour. The solution was concentrated under reduced pressure and then recrystallized from ethyl acetate to obtain 363 mg of (3RS,4RS)-3-(2,4-dichlorophenyl)-N-hydroxy-2-{(1SR,2SR)-2-[(mesyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide as a colorless crystal.

Workup

  1. temperaturecooling
  2. concentrationThe solution was concentrated under reduced pressure
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4941d67e95094ad6889958121ed31442
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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