4-Methylmorpholine → HCID 22106655, compound

HRID 482368Notes

Reaction equation

HRID 482368 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN(C)CCCN=C=NCC.Cl.C[O:32][C:33](=[O:36])[CH2:34][NH2:35].CN1CCOCC1>C(Cl)Cl.C(OCC)(=O)C.Cl.N1C=CC=CC=1.C1COCC1>[C:33]([CH2:34][NH:35][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([OH:36])=[O:32]

Participants

10

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 122755Glycine methyl ester hydrochlorideHCID 170289Benzeneacetic acid, 4-hydroxy-.alpha.-(4-hydroxyphenyl)-

Product 1

HCID 22106655HCID 22106655, compoundYield 90.5%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution in CH2Cl2 (0.5 mL), THF (20 mL), and pyridine (20 mL) of 2,2-bis(4-hydroxyphenyl)acetic acid (0.94 g, 3.85 mmol), prepared as in Example 31, was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.10 g, 5.76 mmol), glycine methyl ester hydrochloride (0.723 g, 5.76 mmol), and N-methylmorpholine (0.63 mL, 5,76 mmol) and the mixture was stirred overnight at room temperature. The reaction mixture was then diluted with ethyl acetate and aqueous 0.5 N HCl. The organic layer was washed with 0.5 N HCl (3X), saturated aqueous NaHCO3 (3X), and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was dried to constant weight on high vacuum to give 1.05 g (87%) of 2,2-bis(4-hydroxyphenyl)acetic acid-N-carboxymethyl amide.

Workup

  1. washThe organic layer was washed with 0.5 N HCl (3X), saturated aqueous NaHCO3 (3X), and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was dried to constant weight on high vacuum

Sources & evidence

ORD record
ord-9a117e4d311446a1bfea6a53ed7c559e
Source dataset
uspto-grants-1998_08
Patent number
US05795900

Reaction notes

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