Trifluoroacetic acid → HCID 19870577, compound

HRID 330185Notes

Reaction equation

HRID 330185 reaction equation
FC(F)(F)[C:3](O)=[O:4].C([O:12][C:13](/[C:15](/[CH3:40])=[CH:16]/[C:17]1[CH:25]=[C:24]2[C:20]([C:21]([CH2:37][CH2:38][CH3:39])=[CH:22][N:23]2[CH2:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=2)=[CH:19][CH:18]=1)=[O:14])(C)(C)C>C(Cl)Cl>[C:13](/[C:15](/[CH3:40])=[CH:16]/[C:17]1[CH:25]=[C:24]2[C:20]([C:21]([CH2:37][CH2:38][CH3:39])=[CH:22][N:23]2[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:35][C:36]=2[O:4][CH3:3])=[CH:19][CH:18]=1)([OH:12])=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19870601HCID 19870601, compound

Product 1

HCID 19870577HCID 19870577, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 ml), pre-cooled to 0°, was added slowly to a stirred solution of methyl E-4-[6-[2-(t-butoxycarbonyl)prop-1-enyl]-3-propylindol-1-ylmethyl]benzoate (1.22 g) in methylene chloride (10 ml) at 0° under an atmosphere of nitrogen. The mixture was stirred at 0° for 1.5 hr, then carefully evaporated at room temperature to give an oil which was crystallized from ether to give methyl E-4-[6-(2-carboxyprop-1-enyl)-3-propylindol-1-ylmethyl]-3-methoxybenzoate (0.94 g, 87%) as a yellow powder; mp 167°-169°; partial NMR (300 MHz, DMSO-d6): 0.94(t, 2H, CH2CH3), 1.65(m, 2H, CH2CH3), 2.03(d, 3H, C(CH3)), 2.65(t, 2H, CH2CH2CH3), 3.82(s, 3H, OCH3), 3.93(s, 3H, OCH3 ), 5.40(s, 2H, NCH2), 12.30(br s, about 1H, COOH).

Workup

  1. customcarefully evaporated at room temperature
  2. customto give an oil which
  3. customwas crystallized from ether

Sources & evidence

ORD record
ord-7cc4b2609e6d493bb5526b6b10432e82
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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