3,5-Dihydroxybenzoic Acid → HCID 54533744, compound

HRID 1155507Notes

Reaction equation

HRID 1155507 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=O.Cl.[CH3:13][O:14][C:15](=[O:26])[C@H:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[NH2:17].ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:13][O:14][C:15](=[O:26])[C@H:16]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[NH:17][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([OH:11])[CH:10]=[C:2]([OH:1])[CH:3]=1

Participants

7

Reactant 5

HCID 74243,5-Dihydroxybenzoic AcidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 76956Methyl tyrosinate hydrochloride

Product 1

HCID 54533744HCID 54533744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

231.2 g of 3,5-dihydroxybenzoic acid are dissolved in 4 l of dimethyl formamide. 313 g of L-tyrosine-methyl ester hydrochloride, 202 g of 1-hydroxybenzotriazole and 346 ml of N-ethyl morpholine and subsequently 297 g of dicyclohexyl carbodiimide are added. The mixture is stirred over night at room temperature, and the precipitated dicyclohexyl urea is filtered off. The solvent is distilled off in vacuo, the residue is taken up in 4 l of ethyl acetate, the ethyl acetate solution is washed 4 times each with saturated sodium bicarbonate solution, 3 times with 400 ml portions of a solution of 5% KHSO4 and 10% K2SO4 and twice with 200 ml portions of water, dried over sodium sulfate and subsequently brought to dryness. Yield: 360 g of resin.

Workup

  1. filtrationthe precipitated dicyclohexyl urea is filtered off
  2. distillationThe solvent is distilled off in vacuo
  3. washthe ethyl acetate solution is washed 4 times each with saturated sodium bicarbonate solution, 3 times with 400 ml portions of a solution of 5% KHSO4 and 10% K2SO4
  4. dry with materialtwice with 200 ml portions of water, dried over sodium sulfate

Sources & evidence

ORD record
ord-59b1e071c50a4b51b292190f81ce430f
Source dataset
uspto-grants-1981_11
Patent number
US04302448

Reaction notes

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