Trifluoroacetic acid → HCID 59432471, compound

HRID 507131Notes

Reaction equation

HRID 507131 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([N:15]([CH2:34][C:35]2[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=2)[C:16]2[N:17]=[N:18][N:19]([CH2:21][CH2:22][N:23]3[C:31](=[O:32])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]3=[O:33])[N:20]=2)[C:10]2[CH:49]=[C:50]([CH3:57])[C:51]([C:53]([F:56])([F:55])[F:54])=[CH:52][C:9]1=2)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[F:48][C:45]([F:46])([F:47])[C:37]1[CH:36]=[C:35]([CH:40]=[C:39]([C:41]([F:42])([F:43])[F:44])[CH:38]=1)[CH2:34][N:15]([C@H:11]1[CH2:12][CH2:13][CH2:14][NH:8][C:9]2[CH:52]=[C:51]([C:53]([F:54])([F:55])[F:56])[C:50]([CH3:57])=[CH:49][C:10]1=2)[C:16]1[N:17]=[N:18][N:19]([CH2:21][CH2:22][N:23]2[C:24](=[O:33])[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]2=[O:32])[N:20]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59432458HCID 59432458, compound

Product 1

HCID 59432471HCID 59432471, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-5-((3,5-Bis-trifluoromethyl-benzyl)-{2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-2H-tetrazol-5-yl}-amino)-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester (0.12 mmol) in dichloromethane (4 mL), add trifluoroacetic acid (1 mL). After stirring at room temperature for 1 h, quench the reaction with concentrated sodium carbonate (10 mL), and dilute with water (10 mL) and dichloromethane (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, to provide the title compound as a colorless foam. MS (ES+): 712 (M+H).

Workup

  1. customquench
  2. customthe reaction with concentrated sodium carbonate (10 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-c3e1c736a6ed46ee930bfb71ae81f202
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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