HCID 86749489, compound → HCID 67737305, compound

HRID 440389Notes

Reaction equation

HRID 440389 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](=[CH:17]/[C:18]2[C:26]3[C:21](=[CH:22][C:23]([Cl:28])=[CH:24][C:25]=3[Cl:27])[N:20]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:19]=2[C:39]([O:41][CH2:42][CH3:43])=[O:40])/[C:10]([O:12]C(C)(C)C)=[O:11])=[CH:5][CH:4]=1>C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[C:9](=[CH:17]/[C:18]2[C:26]3[C:21](=[CH:22][C:23]([Cl:28])=[CH:24][C:25]=3[Cl:27])[N:20]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)(=[O:30])=[O:31])[C:19]=2[C:39]([O:41][CH2:42][CH3:43])=[O:40])/[C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 86749489HCID 86749489, compound

Product 1

HCID 67737305HCID 67737305, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Combine (E) and (Z)-2-(4-methoxyphenyl)-3-(1-p-toluensulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester (427 mg) and 96% formic acid (6 mL). After 24 hours, evaporate in vacuo to obtain a residue and recrystallize that residue, if desired, from cyclohexane/ethyl acetate to obtain the intermediate (E) and (Z)-2-(4-methoxyphenyl)-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid: mp 175°-178° C.; IR (KBr) νmax 1728, 1692, 1371, 1271, 1250, 1179 cm-1 ; 1H NMR (CDCl3) δ8.01 (s, 1H), 7.92 (d, 1H, J=1.7 Hz), 7.63 (d, 2H, J=8.5 Hz), 7.26 (d, 1H, J=1.7 Hz), 7.22 (d, 2H, J=8.5 Hz), 7.01 (d, 2H, J=8.8 Hz), 6.67 (d, 2H, J=8.9 Hz), 4.16 (q, 2H, J= 7.2 Hz), 3.76 (s, 3H), 2.38 (s, 3H), 1.24 (t, 3H, J=7.2 Hz).

Workup

  1. customevaporate in vacuo
  2. customto obtain a residue
  3. customrecrystallize that residue

Sources & evidence

ORD record
ord-f22645c0c9ba4223a45b0140e54d9038
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Reaction notes

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