Triethylamine → Methyl 2-(benzyloxycarbonylamino)-2-(oxetan-3-yl)acetate

HRID 58795Notes

Reaction equation

HRID 58795 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12](=[C:17]1[CH2:20][O:19][CH2:18]1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CO.[Pd]>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:17]1[CH2:20][O:19][CH2:18]1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 57610999Methyl 2-(((benzyloxy)carbonyl)amino)-2-(oxetan-3-ylidene)acetate

Product 1

HCID 59372526Methyl 2-(benzyloxycarbonylamino)-2-(oxetan-3-yl)acetateYield 42.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%, 5.0 g) was added to a solution of methyl 2-(benzyloxycarbonylamino)-2-(oxetan-3-ylidene)acetate (10.0 g, 36 mmol) in MeOH (100 mL). The suspension was stirred under hydrogen atmosphere at ambient temperature for 12 h. The catalyst was filtered off and washed with MeOH (100 mL). The filtrate and washings were combined followed by addition of benzyloxycarbonyl N-succinimide (Cbz-OSu; 10.0 g, 40 mmol) and triethylamine (15.2 mL, 108 mmol). The reaction mixture was stirred for 12 h at ambient temperature and then concentrated. The residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=5:1) to afford methyl 2-(benzyloxycarbonylamino)-2-(oxetan-3-yl)acetate (4.3 g, 41% yield) as a yellow solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH (100 mL)
  3. stirringThe reaction mixture was stirred for 12 h at ambient temperature
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=5:1)

Sources & evidence

ORD record
ord-bbb917469dae4256b41311c53b526cf6
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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