Trifluoroacetic acid → HCID 59787387, compound

HRID 1965984Notes

Reaction equation

HRID 1965984 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59787401HCID 59787401, compound

Product 1

HCID 59787387HCID 59787387, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-[5-(cyclopentanecarbonyl-amino)-pentyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (311 mg, 0.67 mmoles) in dichloromethane (10 mL) and add trifluoroacetic acid (3 mL). Stir the reaction for 1 h. Concentrate in vacuo and purify the residue by preparative HPLC to give 7-chloro-6-[5-(cyclopentanecarbonyl-amino)-pentyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (135 mg) as an oil. Dissolve the oil in methanol (5 mL) and add (L)-tartaric acid (56 mg, 0.37 mmoles). Concentrate the mixture in vacuo and then add water (5 mL). The resulting solution is then freeze dried overnight to yield the title compound as a white solid (184 mg, 55%). MS (ES+) m/z=363.2 (M+H)+.

Workup

  1. customthe reaction for 1 h
  2. concentrationConcentrate in vacuo
  3. custompurify the residue by preparative HPLC

Sources & evidence

ORD record
ord-5c1a20cef71542b2809228ba71de17da
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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