Trifluoroacetic acid → (S)-(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-(2,3,4,5,7,8,9,10-octahydro-1H-naphtho[2,3-b]azepin-5-yl)-amine

HRID 507103Notes

Reaction equation

HRID 507103 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([N:15]([CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[C:16]2[N:17]=[N:18][N:19]([CH3:21])[N:20]=2)[C:10]2[CH:37]=[C:38]3[C:43](=[CH:44][C:9]1=2)[CH2:42][CH2:41][CH2:40][CH2:39]3)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:36][C:33]([F:34])([F:35])[C:25]1[CH:24]=[C:23]([CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=1)[CH2:22][N:15]([C:16]1[N:17]=[N:18][N:19]([CH3:21])[N:20]=1)[C@H:11]1[CH2:12][CH2:13][CH2:14][NH:8][C:9]2[CH:44]=[C:43]3[C:38](=[CH:37][C:10]1=2)[CH2:39][CH2:40][CH2:41][CH2:42]3

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59432518(S)-5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-2,3,4,5,7,8,9,10-octahydro-naphtho[2,3-b]azepine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59432294(S)-(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-(2,3,4,5,7,8,9,10-octahydro-1H-naphtho[2,3-b]azepin-5-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-2,3,4,5,7,8,9,10-octahydro-naphtho[2,3-b]azepine-1-carboxylic acid tert-butyl ester (0.67 mmol) in dichloromethane (18 mL) add trifluoroacetic acid (2 mL). After stirring at room temperature for 1 h, quench with concentrated sodium carbonate (10 mL) and dilute with dichloromethane (20 mL) and water (20 mL). Separate the organic phase and wash the aqueous with dichloromethane (2×10 mL). Dry the combined organics over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the product over silica gel eluting with ethyl acetate/hexane (5-30%) to afford the title compound as a colorless foam. MS (ES+): 525 (M+H).

Workup

  1. customquench with concentrated sodium carbonate (10 mL)
  2. additiondilute with dichloromethane (20 mL) and water (20 mL)
  3. customSeparate the organic phase
  4. washwash the aqueous with dichloromethane (2×10 mL)
  5. dry with materialDry the combined organics over sodium sulfate
  6. filtrationfilter
  7. customremove solvent under vacuum

Sources & evidence

ORD record
ord-44bc5fd7782b47fda497ca8c2f8cb475
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

Loading…