Sodium Hydroxide → 2-Diphenylacetyl-6-methoxy-5-(4-methoxy-3-methyl-benzyloxy)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

HRID 2395852

Reaktionsgleichung

Reaktionsgleichung von HRID 2395852
[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

Komponenten

4

Edukt 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

Produkt 1

HCID 224024342-Diphenylacetyl-6-methoxy-5-(4-methoxy-3-methyl-benzyloxy)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9f3f5af691794db9a87ebf8d0dcff306
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05489686

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