Trifluoroacetic acid → N-[(5S)-3,9,10,11-Tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]-2-[2-aminoacetylamino]acetamide

HRID 1761236Notes

Reaction equation

HRID 1761236 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH:23][C:24](=[O:38])[CH2:25][NH:26][C:27](=[O:37])[CH2:28][NH:29]C(OCCCC)=O)[C:7]=2[CH:39]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH:23][C:24](=[O:38])[CH2:25][NH:26][C:27](=[O:37])[CH2:28][NH2:29])[C:7]=2[CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69732781N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo [a,c]cyclohepten-5-yl]-2-[2-(butoxycarbonylamino)acetylamino]acetamide

Product 1

HCID 9889617N-[(5S)-3,9,10,11-Tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]-2-[2-aminoacetylamino]acetamideYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]-2-[2-(butoxycarbonylamino)acetylamino]acetamide (0.9 g ; 0.64 mmol) in dichloromethane (6 ml) was treated with TFA (6 ml) at ambient temperature for 0.5 hour. After evaporation to dryness, the residue was neutralised to pH 6.5 with solid sodium hydrogen carbonate and purified on reverse phase silica eluting with a gradient of 30-40% methanol/ammonium carbonate buffer (2 g/l, pH 7). The appropriate fractions were evaporated to dryness and triturated in ether to give the title compound.

Workup

  1. customAfter evaporation to dryness
  2. custompurified on reverse phase silica eluting with a gradient of 30-40% methanol/ammonium carbonate buffer (2 g/l, pH 7)
  3. customThe appropriate fractions were evaporated to dryness
  4. customtriturated in ether

Sources & evidence

ORD record
ord-e65fb4047a0f4a2a99993c17caec12f4
Source dataset
uspto-grants-2005_01
Patent number
US06846925B2

Reaction notes

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