5-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid → 5-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid t-butyl ester

HRID 2166368Notes

Reaction equation

HRID 2166368 reaction equation
[O:1]([C:8]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:9]=1[C:10]1[C:11]([CH2:24][O:25][CH3:26])=[C:12]([C:21]([OH:23])=[O:22])[N:13]=[CH:14][C:15]=1[NH:16]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[C:9]([O:22][C:21]([C:12]1[N:13]=[CH:14][C:15]2[NH:16][C:17]3[C:9]([C:10]=2[C:11]=1[CH2:24][O:25][CH3:26])=[C:8]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:20]=[CH:19][CH:18]=3)=[O:23])([CH3:17])([CH3:10])[CH3:8]

Participants

3

Reactant 1

HCID 230394415-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid

Product 1

HCID 138001155-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid t-butyl esterYield 74.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

300 mg of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid is heated with 2 ml of aminal ester for 3 hours to 120° C., whereby a solution is produced. After diluting with water, it is extracted with ethyl acetate. The organic phase is dreid, filtered, concentrated and chromatographed over silica gel with acetone:hexane=1:1 as eluant. 130 mg of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid t-butyl ester with a decomposition point of 150° C. is obtained.

Workup

  1. customis produced
  2. extractionis extracted with ethyl acetate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed over silica gel with acetone

Sources & evidence

ORD record
ord-5a4bcacb772c42b1b6ec568f0c17e695
Source dataset
uspto-grants-1990_07
Patent number
US04945090

Reaction notes

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