3-Hydroxyazetidine → HCID 86590882, compound

HRID 891801Notes

Reaction equation

HRID 891801 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([N:24]=[C:25]=[S:26])[CH2:5][O:6][Si:7]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:28][CH:29]1[CH2:32][NH:31][CH2:30]1>O1CCCC1.O>[CH3:1][O:2][C:3](=[O:27])[C@@H:4]([NH:24][C:25]([N:31]1[CH2:32][CH:29]([OH:28])[CH2:30]1)=[S:26])[CH2:5][O:6][Si:7]([C:20]([CH3:23])([CH3:21])[CH3:22])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 15142903-HydroxyazetidineHCID 86590883HCID 86590883, compound

Product 1

HCID 86590882HCID 86590882, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(t-butyldiphenylsilyloxy)-2-isothiocyanatopropionic acid methyl ester (13.4 g, 33.5 mmol) (obtained as described in Reference Example 70(1)) in tetrahydrofuran (245 ml) was added a solution of 3-hydroxyazetidine (4.90 g, 67.1 mmol) (obtained as described in Reference Example 31(1)) in water (50 ml) at room temperature and the mixture was stirred overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene and toluene:acetonitrile (3:1) as the eluant to afford (2S)-3-(t-butyldiphenylsilyloxy)-2-[(3-hydroxyazetidine-1-carbothioyl)amino]propionic acid methyl ester (9.60 g, yield 61%) as an yellow solid.

Workup

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-ae3948d98d2e441e84fa584781c0593c
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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