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

HRID 1417963Notes

Reaction equation

HRID 1417963 reaction equation
CC([O:4][C:5]([C:7]1[N:44]=[CH:43][C:10]2[N:11]([CH2:26][C:27](=[O:42])[CH2:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:41])[CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:12]3[C:17]([C:9]=2[C:8]=1[CH2:45][O:46][CH3:47])=[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](=[O:42])[CH2:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:41])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]1[CH:43]=[N:44][C:7]([C:5]([OH:6])=[O:4])=[C:8]([CH2:45][O:46][CH3:47])[C:9]2=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867538596-benzyloxy-4-methoxymethyl-9{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

Product 1

HCID 442135056-benzyloxy-4-methoxymethyl-9-{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}-9H-pyrido-[3,4-b]-indole-3-carboxylic acidYield 64.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

350 mg of 6-benzyloxy-4-methoxymethyl-9-{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester (0.55 mmol) is mixed in 10 ml of methanol with 1 ml of 2N aqueous sodium hydroxide solution and held at 40° C. until the reaction is completed. Then, the reaction mixture is acidified with dilute hydrochloric acid, and the precipitated product is suctioned off. It is washed with water and then with diethyl ether, dried in a vacuum, and 212 mg of 6-benzyloxy-4-methoxymethyl-9-{6-[N-methyl-N-(2-phenylethyl)-amino]-2-oxohexyl}-9H-pyrido-[3,4-b]-indole-3-carboxylic acid is obtained as a yellow, amorphous powder.

Workup

  1. customheld at 40° C. until the reaction
  2. washIt is washed with water
  3. dry with materialwith diethyl ether, dried in a vacuum

Sources & evidence

ORD record
ord-147b6912136349b2b8a9803151fcff91
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

Loading…