HCID 22603421, compound → HCID 22603444, compound

HRID 2307926Notes

Reaction equation

HRID 2307926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH2:16][CH:17]2[CH2:21][O:20]C(C)(C)[O:18]2)=[C:7]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH2:16][CH:17]([OH:18])[CH2:21][OH:20])=[C:7]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 1

HCID 22603421HCID 22603421, compound2×

Product 1

HCID 22603444HCID 22603444, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl N-(3,4-dichlorobenzyl)-3-(2,2-dimethyl-1,3-dioxolane-4-ylmethoxy)-indole-2-carboxylate [Compound 70] (15.92 g) was dissolved in tetrahydrofuran (70 ml) and hydrochloric acid (4M, 33 ml), and stirred at ambient temperature for 4 hours. The reaction was concentrated in vacuo, added to water (200 ml) and extracted with ethyl acetate (3×200 ml). The combined organic extracts were dried (MgSO4), and concentrated in vacuo, and the residue purified by column chromatography using 70% ethyl acetate:iso-hexane as eluent, to afford the product as a dark yellow oil that crystallised upon standing to off white crystals (9.37 g, 65%); NMR d (CD3SOCD3)1.27 (t, 3H), 3.50 (m, 2H), 3.83 (m, 1H), 4.08 (m, 1H), 4.20 (m, 1H), 4.27 (q, 2H), 4.58 (t, 1H), 4.88 (d, 1H), 5.73 (s, 2H), 6.88 (d, 1H), 7.15 (t, 1H), 7.33 (m, 2H), 7.54 (m, 2H), 7.82 (d, 1H), M/z (+) 438.3 (MH+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionadded to water (200 ml)
  3. extractionextracted with ethyl acetate (3×200 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-698e8e1d1f944b2babb74078d4cf7795
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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