Methanol → HCID 18522130, compound

HRID 413799Notes

Reaction equation

HRID 413799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:21]([O:23]CC)=[O:22].CO.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18522114HCID 18522114, compound

Product 1

HCID 18522130HCID 18522130, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl N-(3,4-dichlorobenzyl)-4-(2,3-dihydroxypropoxy)indole-2-carboxylate (85 mg) was dissolved in THF (3 ml) and methanol (1 ml) and sodium hydroxide (2M, 3.0 ml) was added and the reaction stirred for 16 hours. The reaction was then concentrated in vacuo and the residue dissolved in water. The solution was acidified by dropwise addition of acetic acid, resulting in the precipitation of a white solid which was filtered, washed with water and dried in vacuo to give the desired end product (70 mg, 81%); NMR d (CD3SOCD3) 3.40-3.53 (m, 3H), 3.98-4.10 (m, 2H), 5.80 (s, 2H), 6.59 (d, 1H), 6.88 (d, 1H), 7.09 (d, 1H), 7.20 (t, 1H), 7.30 (d, 1H), 7.36 (s, 1H), 7.51 (d, 1H); M/z (−) 408 (M−H+).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. dissolutionthe residue dissolved in water
  3. additionThe solution was acidified by dropwise addition of acetic acid
  4. customresulting in the precipitation of a white solid which
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6311188fc43a4c6a8b42b0c43c545f6e
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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