Trifluoroacetic acid → HCID 178421834, compound

HRID 507040Notes

Reaction equation

HRID 507040 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:21][CH2:20][CH2:19][CH:18]([N:22]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[C:23]2[NH:27][N:26]=[N:25][N:24]=2)[C:17]2[CH:43]=[C:44]([CH3:51])[C:45]([C:47]([F:50])([F:49])[F:48])=[CH:46][C:16]1=2)=O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:42][C:39]([F:40])([F:41])[C:31]1[CH:30]=[C:29]([CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=1)[CH2:28][N:22]([CH:18]1[CH2:19][CH2:20][CH2:21][NH:15][C:16]2[CH:46]=[C:45]([C:47]([F:48])([F:49])[F:50])[C:44]([CH3:51])=[CH:43][C:17]1=2)[C:23]1[NH:27][N:26]=[N:25][N:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 178421835HCID 178421835, compound

Product 1

HCID 178421834HCID 178421834, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add dichloromethane (5 mL) and trifluoroacetic acid (5 mL) to 5-[(3,5-bis-trifluoromethyl-benzyl)-(1H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester (0.18 g, 0.24 mmol). After stirring for 1-2 h, neutralize the reaction with sodium carbonate. Wash the organic phase with water (5 mL) and brine (5 mL). Dry the organics over sodium sulfate and filter. Chromatograph the crude material, eluting with ethyl acetate/hexane (20-60%) to provide the title compound (0.13 g, 85%) as an oil. MS (ES+): 539 (M+H).

Workup

  1. washWash the organic phase with water (5 mL) and brine (5 mL)
  2. dry with materialDry the organics over sodium sulfate
  3. filtrationfilter
  4. washChromatograph the crude material, eluting with ethyl acetate/hexane (20-60%)

Sources & evidence

ORD record
ord-0c006f19d12c480baa2f915275736ddc
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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