Trifluoroacetic acid → (S)-3-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4-(isoquinolin-3-ylcarbamoyloxy)butanoic acid

HRID 416444Notes

Reaction equation

HRID 416444 reaction equation
[Cl:1][C:2]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][NH:5][C:6](=[O:33])[N:7]([C@H:9]([CH2:18][O:19][C:20](=[O:32])[NH:21][C:22]1[N:23]=[CH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])[CH3:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][NH:5][C:6](=[O:33])[N:7]([C@H:9]([CH2:18][O:19][C:20](=[O:32])[NH:21][C:22]1[N:23]=[CH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:10][C:11]([OH:13])=[O:12])[CH3:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57947781(S)-tert-butyl 3-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4-(isoquinolin-3-ylcarbamoyloxy)butanoate

Product 1

HCID 57947837(S)-3-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4-(isoquinolin-3-ylcarbamoyloxy)butanoic acidYield 180.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-tert-butyl 3-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4-(isoquinolin-3-ylcarbamoyloxy)butanoate (0.8 g, 1.47 mmol) and DCM (10 mL) was added TFA (10 mL). The resulting solution was stirred at RT for 1 h. The mixture was concentrated, and the remaining residue was dried in vacuo to give (S)-3-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4-(isoquinolin-3-ylcarbamoyloxy)butanoic acid (1.3 g), which was used without further purification. LRMS (M+H+) m/z 489.1.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe remaining residue was dried in vacuo

Sources & evidence

ORD record
ord-f2b6f6522367429282100480a2056df6
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

Loading…