(RS)-5-[(4-Carbomethoxyphenyl)methoxy]-2-(diphenyacetyl)-1,2,3,4-tetrahydro-6-methoxy-3-isoquinolinecarboxylic acid, ethyl ester → HCID 15296726, compound

HRID 5899Notes

Reaction equation

HRID 5899 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]3[C:14]=2[CH2:15][CH:16]([C:40]([O:42]CC)=[O:41])[N:17]([C:25](=[O:39])[CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18]3)=[CH:7][CH:6]=1)([O:3]C)=[O:2]>CO.[OH-].[Na+]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]3[C:14]=2[CH2:15][CH:16]([C:40]([OH:42])=[O:41])[N:17]([C:25](=[O:39])[CH:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18]3)=[CH:7][CH:6]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 15296730(RS)-5-[(4-Carbomethoxyphenyl)methoxy]-2-(diphenyacetyl)-1,2,3,4-tetrahydro-6-methoxy-3-isoquinolinecarboxylic acid, ethyl ester

Product 1

HCID 15296726HCID 15296726, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.10 g (0.0019 mole) of the diester from Example 32 in 100 mL of methanol and 15 mL of 2N sodium hydroxide is heated to the boiling point, allowing the methanol to distill off. After 1 hour (pot temperature =90° C.), 1N hydrochloric acid (35 mL) is added to precipitate a gum. On addition of 10 mL of ether, crystals develop; wt. 0.84 g. Recrystallization from ethyl acetate petroleum ether gives pure product; mp 190°-192° C.

Workup

  1. distillationto distill off
  2. additionAfter 1 hour (pot temperature =90° C.), 1N hydrochloric acid (35 mL) is added
  3. customto precipitate a gum
  4. additionOn addition of 10 mL of ether, crystals
  5. customRecrystallization from ethyl acetate petroleum ether
  6. customgives pure product

Sources & evidence

ORD record
ord-7bee3f2deba042d7930137633227fc6b
Source dataset
uspto-grants-1993_09
Patent number
US05246943

Reaction notes

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