Hydrochloric Acid → 6-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid

HRID 1417961Notes

Reaction equation

HRID 1417961 reaction equation
CC([O:4][C:5]([C:7]1[N:40]=[CH:39][C:10]2[N:11]([CH2:26][C:27]([N:29]([CH3:38])[CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:28])[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:41][O:42][CH3:43])=[CH:16][C:15]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:14][CH:13]=3)=[O:6])C.[OH-].[Na+].Cl>CO>[CH2:19]([O:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:26][C:27]([N:29]([CH3:38])[CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:28])[C:10]1[CH:39]=[N:40][C:7]([C:5]([OH:6])=[O:4])=[C:8]([CH2:41][O:42][CH3:43])[C:9]2=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98083526-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

Product 1

HCID 867538586-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acidYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

211 mg of 6-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is mixed in 1 ml of methanol with 0.5 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 yellow reaction product is suctioned off, washed with water and diethyl ether and dried in a vacuum. 150 mg of 6-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid is obtained.

Workup

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

Sources & evidence

ORD record
ord-62adfd4ddd5144168cae9c98dd01973c
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

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