Ethanol → 5-Benzyloxy-4-methoxymethyl-betacarboline-3-carboxylic acid isopropyl ester

HRID 36334Notes

Reaction equation

HRID 36334 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:10]=1[C:11]1[C:12]([CH2:25][O:26][CH3:27])=[C:13]([C:22]([OH:24])=[O:23])[N:14]=[CH:15][C:16]=1[NH:17]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:29](=O)([O-])[O-].[Cs+].[Cs+].[CH2:35](O)[CH3:36]>>[CH:35]([O:23][C:22]([C:13]1[N:14]=[CH:15][C:16]2[NH:17][C:18]3[C:10]([C:11]=2[C:12]=1[CH2:25][O:26][CH3:27])=[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:21]=[CH:20][CH:19]=3)=[O:24])([CH3:36])[CH3:29]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10796Cesium carbonateHCID 214629345-Benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylic acid

Product 1

HCID 541385905-Benzyloxy-4-methoxymethyl-betacarboline-3-carboxylic acid isopropyl ester

Procedure

740 mg (2 mmol) of 5-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid is stirred for 2 hours at 80° C. in 50 ml of ethanol and 20 ml of water with 977 mg of cesium carbonate. After concentration on a rotary evaporator and drying in a desiccator, the mixture is taken up in 50 ml of DMF, combined with 0.2 ml of 2-bromopropane, and heated for 8 hours to 60°-70° C. After concentration, the mixture is chromatographed over silica gel with hexane:acetone=1:1 as the eluent, thus obtaining 340 mg of 5-benzyloxy-4-methoxymethyl-βcarboline-3-carboxylic acid isopropyl ester having the above-mentioned melting point.

Workup

  1. concentrationAfter concentration
  2. customon a rotary evaporator
  3. customdrying in a desiccator
  4. temperatureheated for 8 hours to 60°-70° C
  5. concentrationAfter concentration
  6. customthe mixture is chromatographed over silica gel with hexane

Sources & evidence

ORD record
ord-0c52309a4cf14a928822d3b8a07e94b3
Source dataset
uspto-grants-1995_05
Patent number
US05414002

Reaction notes

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