Sulfuric Acid → HCID 15342540, compound

HRID 1417966Notes

Reaction equation

HRID 1417966 reaction equation
[OH-].[Li+].CC([O:6][C:7]([C:9]1[N:44]=[CH:43][C:12]2[N:13]([CH2:30][C:31]([N:33]([CH3:42])[CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:32])[C:14]3[C:19]([C:11]=2[C:10]=1[CH2:45][O:46][CH3:47])=[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)[CH:17]=[CH:16][CH:15]=3)=[O:8])C.S(=O)(=O)(O)O>CO.O1CCCC1.C(OCC)(=O)C>[CH3:47][O:46][CH2:45][C:10]1[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[N:13]([CH2:30][C:31]([N:33]([CH3:42])[CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:32])[C:12]=2[CH:43]=[N:44][C:9]=1[C:7]([OH:8])=[O:6]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 15342539HCID 15342539, compound

Product 1

HCID 15342540HCID 15342540, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

10 ml of an aqueous 0.5N lithium hydroxide solution is added to a solution of 610 mg of 4-methoxymethyl-5-(4-nitrophenoxy)-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid (1-methyl-ethyl)-ester in 10 ml of methanol and 10 ml of tetrahydrofuran, and it is stirred for 24 hours at 50° C. Then, it is cooled to 20° C., acidified with 10% aqueous sulfuric acid and diluted with ethyl acetate. The solution that is obtained is washed twice with saturated sodium chloride solution dried on sodium sulfate and evaporated to dryness in a vacuum. The crude product that is obtained is recrystallized from ethanol/tetrahydrofuran, and 360 mg of 4-methoxymethyl-5-(4-nitrophenoxy)-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid is obtained as pale yellowish crystals with a melting point of 231°-232° C.

Workup

  1. temperatureThen, it is cooled to 20° C.
  2. customThe solution that is obtained
  3. washis washed twice with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. customevaporated to dryness in a vacuum
  6. customThe crude product that is obtained
  7. customis recrystallized from ethanol/tetrahydrofuran

Sources & evidence

ORD record
ord-849ec9779ee740ad928388f295192f50
Source dataset
uspto-grants-1999_03
Patent number
US05880126

Reaction notes

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