Tetrahydrofuran → N-methoxycarbonyl-O-methyl-L-tyrosine

HRID 274089Notes

Reaction equation

HRID 274089 reaction equation
C([O:8][C:9](=[O:25])[C@H:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[NH:11][C:12]([O:14][CH3:15])=[O:13])C1C=CC=CC=1.O1CCCC1>[Pd].O>[CH3:15][O:14][C:12]([NH:11][C@H:10]([C:9]([OH:25])=[O:8])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[O:13]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 54335584N-methoxycarbonyl-O-methyl-L-tyrosine benzyl ester

Product 1

HCID 54533786N-methoxycarbonyl-O-methyl-L-tyrosineYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 962WaterSolvent

Procedure

A mixture of N-methoxycarbonyl-O-methyl-L-tyrosine benzyl ester (14.5 g), 10% palladium on carbon (0.73 g), and tetrahydrofuran (145 ml)-water (14.5 ml) was shaken under hydrogen at ambient temperature for 2 hours. An additional 10% palladium on carbon (0.73 g) was added to the mixture and shaking was continued for an additional 2 hours. The catalyst was filtered off and washed with tetrahydrofuran. The filtrate and washings were combined and concentrated in vacuo to afford N-methoxycarbonyl-O-methyl-L-tyrosine (10.5 g).

Workup

  1. stirringshaking
  2. waitwas continued for an additional 2 hours
  3. filtrationThe catalyst was filtered off
  4. washwashed with tetrahydrofuran
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f12865195d494aac8c7bb83f19df5441
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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