2,2-dimethoxyethyl N-benzyloxycarbonylglycine → 2,2-Dimethoxyethyl glycine

HRID 39249Notes

Reaction equation

HRID 39249 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][N:5](C(OCC1C=CC=CC=1)=O)[CH2:6][C:7]([OH:9])=[O:8]>C1COCC1.[Pd]>[CH3:21][O:20][CH:3]([O:2][CH3:1])[CH2:4][NH:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 671854852,2-dimethoxyethyl N-benzyloxycarbonylglycine

Product 1

HCID 193615392,2-Dimethoxyethyl glycineYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 37 (425 mg, 1.43 mmol) dissolved in 20 mL of anhydrous THF in a Parr apparatus for hydrogenation, was added 160 mg of 10% Pd/C, the system was charged with 60 psi of H2, and the bottle was shaken for 2 h. The catalyst was filtered over Celite, washed with 20 mL of ethyl acetate and the combined filtrate was concentrated in vacuo to give 38 (180 mg, 77%). 1H NMR (400 MHz, CDCl3) δ 3.36 (s, 6H), 3.42 (s, 2H), 4.08 (d, J=5.3 Hz, 2H), 4.54 (t, J=5.3 Hz, 1H).

Workup

  1. additionthe system was charged with 60 psi of H2
  2. filtrationThe catalyst was filtered over Celite
  3. washwashed with 20 mL of ethyl acetate
  4. concentrationthe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3fb39e9d7c8241268885ef176626c218
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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