Ethyl Acetate → HCID 86743686, compound

HRID 329962Notes

Reaction equation

HRID 329962 reaction equation
C(OC(=O)[CH:5]([NH2:27])[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])C.O.[C:30]([OH:34])(=[O:33])[CH:31]=O.[C:35](=O)([O-])[O-:36].[K+].[K+].C([O:44][CH2:45][CH3:46])(=O)C>O>[CH2:20]([O:19][C:17]1[C:16](=[C:35]=[O:36])[CH:15]=[CH:14][C:13]2[C:18]=1[C:10]1[CH:6]([CH2:7][O:8][CH3:9])[CH:5]([O:44][CH2:45][CH3:46])[NH:27][CH:31]([C:30]([OH:34])=[O:33])[C:11]=1[N:12]=2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 13133988HCID 13133988, compoundHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 86743686HCID 86743686, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

37.6 g of 3-(4-benzyloxyindol-3-yl)-2-amino-5-oxahexanoic acid ethyl ester is dissolved in 200 ml of ethyl acetate. Under vigorous agitation, a solution of 10.8 g of glyoxylic acid monohydrate in 120 ml of water is added dropwise thereto. The reaction mixture is subsequently adjusted to pH 4 with 10% potassium carbonate solution and stirred for 14 hours at room temperature. The thus-precipitated yellow crystallized product is vacuum-filtered, washed with ethyl acetate, and dried, thus obtaining 20.3 g of 5-benzyloxy-4-methoxymethyl-3-ethoxy-carbonyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid as light-yellow crystals, mp 139°-142°C.

Workup

  1. filtrationThe thus-precipitated yellow crystallized product is vacuum-filtered
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-7ad640405f244c62b9a60c9d7f97bfff
Source dataset
uspto-grants-1990_01
Patent number
US04894377

Reaction notes

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