Hydrochloric Acid → HCID 15342534, compound

HRID 1417964Notes

Reaction equation

HRID 1417964 reaction equation
CC([O:4][C:5]([C:7]1[N:39]=[CH:38][C:10]2[N:11]([CH2:26][C:27]([N:29]([CH3:37])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:40][O:41][CH3:42])=[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15]=[CH:14][CH:13]=3)=[O:6])C.[OH-].[Na+].Cl>CO>[CH2:19]([O:18][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[C:9]1[C:8]([CH2:40][O:41][CH3:42])=[C:7]([C:5]([OH:6])=[O:4])[N:39]=[CH:38][C:10]=1[N:11]2[CH2:26][C:27]([N:29]([CH3:37])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15342533HCID 15342533, compound

Product 1

HCID 15342534HCID 15342534, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

460 mg of 5-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-benzyl-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is mixed in 3 ml of methanol with 1 ml of aqueous 2N sodium hydroxide solution and held at 40° C. until the reaction is completed. Then, the reaction mixture is acidified with dilute hydrochloric acid, the precipitated reaction product is suctioned off, washed with water and diethyl ether and dried in a vacuum. 370 mg of 5-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-benzyl-amino]-2-oxoethyl}-9H-pyrido-[3,4-b]indole-3-carboxylic acid (decomposition starting at 239°) is obtained.

Workup

  1. customheld at 40° C. until the reaction
  2. customthe precipitated reaction product
  3. washwashed with water and diethyl ether
  4. customdried in a vacuum

Sources & evidence

ORD record
ord-80ab3d282a1142128a48aea9093bf0d2
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

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