Sodium Hydroxide → HCID 22402434, compound

HRID 260080

Reaction equation

HRID 260080 reaction equation
[C:1]1([CH:7]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:8]([N:10]2[CH:19]([C:20]([O:22]CC)=[O:21])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:36][CH3:37])[C:16]=3[O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([CH3:35])[CH:28]=3)[CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:38]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([N:10]2[CH:19]([C:20]([OH:22])=[O:21])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:36][CH3:37])[C:16]=3[O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([CH3:35])[CH:28]=3)[CH2:11]2)=[O:9])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15230314(RS)-2-(Diphenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-5-[(4-methoxy-3-methylphenyl)methoxy]-3-isoquinolinecarboxylic acid, ethyl ester

Product 1

HCID 22402434HCID 22402434, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound is prepared by a hydrolysis of the ester from Example 34 as follows: a solution of 0.50 g (0.86 mmole) of the ester, 50 mL of methanol, and 2.0 mL of 1N sodium hydroxide is maintained at reflux for 15 minutes. The methanol is removed, water (30 mL) is added, and 1.0 mL of glacial acetic acid is added to precipitate the gummy product. Purification by silica gel chromatography eluting with 5% methanol-chloroform gives pure product; mp 140°-142° C.

Workup

  1. temperatureat reflux for 15 minutes
  2. customThe methanol is removed
  3. additionwater (30 mL) is added
  4. addition1.0 mL of glacial acetic acid is added
  5. customto precipitate the gummy product
  6. customPurification by silica gel chromatography
  7. washeluting with 5% methanol-chloroform
  8. customgives pure product

Sources & evidence

ORD record
ord-799a8eeae5f74a638d99478050b6a604
Source dataset
uspto-grants-1996_06
Patent number
US05525614

Linked notes

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