Trifluoroacetic acid → 4-(2,3,4,5-Tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid methyl ester

HRID 222650Notes

Reaction equation

HRID 222650 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29][CH3:30])=[O:28])=[CH:23][CH:22]=3)[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:30][O:29][C:27](=[O:28])[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:11]3[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=3[CH:15]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 592579207-(4-Methoxycarbonyl-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

Product 1

HCID 592579194-(2,3,4,5-Tetrahydro-1H-benzo[d]azepin-7-yloxymethyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(4-Methoxycarbonyl-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester (D3) (6.35 g) was dissolved in dichloromethane (30 ml) and treated with trifluoroacetic acid (30 ml). The solution was stirred at room temperature for 2 hours, concentrated in vacuo and then twice co-evaporated with dichloromethane. The residue was dissolved in dichloromethane and washed with 10% aqueous sodium hydroxide, water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford the title compound (D4).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with 10% aqueous sodium hydroxide, water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8136ef0015e448bf8446edc9d2c42224
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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