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Trifluoroacetic acid → 3-[4-(2-{4-[(2,3-Dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyric acid

HRID 1167806
Notes
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Reaction equation

HRID 1167806 reaction equation
[N:1]1([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:38])[CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])=[CH:25][CH:24]=3)=[O:21])=[CH:15][C:14]=2[O:39][CH3:40])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[N:1]1([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([CH:29]([CH3:38])[CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:28]=3)=[O:21])=[CH:15][C:14]=2[O:39][CH3:40])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 22994266Tert-butyl 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

Product 1

HCID 98700693-[4-(2-{4-[(2,3-Dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyric acidYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate [580 mg, Reference Example 1(a)] in dichloromethane (20 ml) was treated with treated with trifluoroacetic acid (1 ml). After 2 hours at room temperature further (1 ml) trifluoroacetic acid was added and the solution was then kept at room temperature overnight. The reaction mixture was evaporated and the residue was suspended in water. This suspension was treated with 1.0 M sodium hydroxide solution (5 ml) and then washed twice with ethyl acetate, then acidified to pH 1 with hydrochloric acid and then filtered. The resultant white solid was washed with water then dried to give the title compound (450 mg) as a white powder, m.p. 152-154° C. [Elemental analysis: C, 67.35; H, 6.02; N, 8.46%. Calculated for C28H29N3O5.0.63H2O: C, 67.41; H, 6.11; N, 8.42%].

Workup

  1. customThe reaction mixture was evaporated
  2. additionThis suspension was treated with 1.0 M sodium hydroxide solution (5 ml)
  3. washwashed twice with ethyl acetate
  4. filtrationfiltered
  5. washThe resultant white solid was washed with water
  6. customthen dried

Sources & evidence

ORD record
ord-ccd4d5d0ae19416099aab773f5ac4296
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06620832B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes