Trifluoroacetic acid → HCID 11541960, compound

HRID 507127Notes

Reaction equation

HRID 507127 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:21][CH2:20][CH2:19][C@H:18]([N:22]([CH2:29][C:30]3[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]=3)[C:23]3[N:24]=[N:25][N:26]([CH3:28])[N:27]=3)[C:17]3[CH:44]=[C:45]([CH3:52])[C:46]([C:48]([F:51])([F:50])[F:49])=[CH:47][C:16]2=3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:35]=[C:30]([CH:31]=[C:32]([C:40]([F:41])([F:42])[F:43])[CH:33]=1)[CH2:29][N:22]([C@H:18]1[CH2:19][CH2:20][CH2:21][N:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:16]2[CH:47]=[C:46]([C:48]([F:49])([F:50])[F:51])[C:45]([CH3:52])=[CH:44][C:17]1=2)[C:23]1[N:24]=[N:25][N:26]([CH3:28])[N:27]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59432372HCID 59432372, compound

Product 1

HCID 11541960HCID 11541960, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-4-{5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl}-piperidine-1-carboxylic acid tert-butyl ester (0.09) in dichloromethane (10 mL), add trifluoroacetic acid (2 mL). After stirring for 1 h at room temperature, quench the reaction with concentrated sodium carbonate (10 mL) and dilute with dichloromethane (20 mL) and water (20 mL). Separate the organics and wash the aqueous with dichloromethane (2×10 mL). Dry the combined organics over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the reaction over silica gel eluting with methanol/dichloromethane (0-5%) to afford the title compound as a colorless foam. MS (ES+): 650 (M+H).

Workup

  1. customquench
  2. customthe reaction with concentrated sodium carbonate (10 mL)
  3. customSeparate the organics and
  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
  8. customChromatograph the reaction over silica gel eluting with methanol/dichloromethane (0-5%)

Sources & evidence

ORD record
ord-f2504078c4794a179c339b84bac1b201
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

Loading…