Water → HCID 67830811, compound

HRID 1708872Notes

Reaction equation

HRID 1708872 reaction equation
C([O:8][C:9](=[O:35])[CH2:10][NH:11][C:12]([C@H:14]1[CH2:17][C@@H:16]([C:18]([O:20]CC2C=CC=CC=2)=[O:19])[N:15]1CC1C=CC=CC=1)=[O:13])C1C=CC=CC=1.O.[H][H]>CO>[C:18]([C@H:16]1[NH:15][C@@H:14]([C:12]([NH:11][CH2:10][C:9]([OH:35])=[O:8])=[O:13])[CH2:17]1)([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 962Water2×HCID 67830946HCID 67830946, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67830811HCID 67830811, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

18.5 mg (39 μmol) of N-[cis-N-benzyl-4-(benzyloxycarbonyl)azetidine-2-carbonyl]glycine benzyl ester in 10 ml of methanol is hydrogenated in a Parr shaker over 34.5 mg of 20% Pd (OH)2 /C (containing 31 % of water) under 4 atm of hydrogen for 4h, 5 ml of water is added, the catalyst is removed by filtration through a double paper filter and washed thoroughly with methanol/water (2:1), and the solution is evaporated. Filtration over SiO2 (isopropanol/water/conc ammonia 14:5:1), evaporation and drying in a vacuum desiccator over P2O5 and KOH affords 6.7 mg (85%) of N-(cis-4-carboxyazetidine-2-carbonyl)glycine as a colorless glass. 1H NMR (D2O):δ4.98 (t, 1H, J =8.5), 4.73 (t, 1H, overlapping), 3.86, 3.74 (AB system, 2H, J =17.5), 3.08 (dt, 1H, J =11.5 (d), 10 (t)), 2.55 (dt, 1H, J =I2 (d), 8.5 (t)).

Workup

  1. additionis added
  2. customthe catalyst is removed by filtration through a double paper
  3. filtrationfilter
  4. washwashed thoroughly with methanol/water (2:1)
  5. customthe solution is evaporated
  6. filtrationFiltration
  7. customover SiO2 (isopropanol/water/conc ammonia 14:5:1), evaporation
  8. dry with materialdrying in a vacuum desiccator over P2O5 and KOH

Sources & evidence

ORD record
ord-2eb3cbad0b5d417197bf0496b54b1f0c
Source dataset
uspto-grants-1990_08
Patent number
US04946839

Reaction notes

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