Trifluoroacetic acid → HCID 59432393, compound

HRID 507059Notes

Reaction equation

HRID 507059 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:21][CH2:20][CH2:19][C@H:18]([N:22]([CH2:29][C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=2)[C:23]2[N:24]=[N:25][N:26]([CH3:28])[N:27]=2)[C:17]2[CH:44]=[C:45]([CH2:52][CH3:53])[C:46]([C:48]([F:51])([F:50])[F:49])=[CH:47][C:16]1=2)=O)(C)(C)C>ClCCl>[F:42][C:40]([F:41])([F:43])[C:32]1[CH:31]=[C:30]([CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=1)[CH2:29][N:22]([C:23]1[N:24]=[N:25][N:26]([CH3:28])[N:27]=1)[C@H:18]1[CH2:19][CH2:20][CH2:21][NH:15][C:16]2[CH:47]=[C:46]([C:48]([F:49])([F:50])[F:51])[C:45]([CH2:52][CH3:53])=[CH:44][C:17]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59432396HCID 59432396, compound

Product 1

HCID 59432393HCID 59432393, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add trifluoroacetic acid (1 mL) to a solution of (S)-5-[(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)amino]-7-ethyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid tert-butyl ester (2.04 g, 3.13 mmol) in dichloromethane (1 mL). Stir for 30 minutes at room temperature. Dilute the mixture with dichloromethane (40 mL) and wash with saturated aqueous sodium bicarbonate solution (40 mL). Dry organic layer over anhydrous sodium sulfate and filter. Remove the solvent under reduced pressure. Purify the residue by column chromatography on silica gel, eluting with ethyl acetate/hexanes (0-30%), to provide the title compound (0.318 g, 98%). MS (ES+): 567 (M+H).

Workup

  1. washwash with saturated aqueous sodium bicarbonate solution (40 mL)
  2. filtrationDry organic layer over anhydrous sodium sulfate and filter
  3. customRemove the solvent under reduced pressure
  4. customPurify the residue by column chromatography on silica gel
  5. washeluting with ethyl acetate/hexanes (0-30%)

Sources & evidence

ORD record
ord-10c8a43cc41b472abcb3803e368ba197
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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