Stannane, hydroxytrimethyl- → HCID 86702706, compound

HRID 1751357Notes

Reaction equation

HRID 1751357 reaction equation
C[O:2][C:3](=[O:16])[C@@H:4]([NH:11][C:12]([O:14][CH3:15])=[O:13])[C@H:5]([O:7][CH:8]([F:10])[F:9])[CH3:6].[OH-].C[Sn+](C)C>ClC(Cl)C.C(OCC)(=O)C>[F:9][CH:8]([F:10])[O:7][C@H:5]([CH3:6])[C@H:4]([NH:11][C:12]([O:14][CH3:15])=[O:13])[C:3]([OH:16])=[O:2]

Participants

5

Reactant 2

HCID 11217597Stannane, hydroxytrimethyl-HCID 59610741(2S,3R)-methyl-3-(difluoromethoxy)-2-(methoxycarbonylamino)butanoate

Product 1

HCID 86702706HCID 86702706, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2S,3R)-methyl-3-(difluoromethoxy)-2-(methoxycarbonylamino)butanoate (265 mg, 1.1 mmol) in dichloroethane (10 mL) was added trimethyltin hydroxide (1 g, 5.5 mmol) and the resulting mixture was heated to 80° C. for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate, washed twice with 5% aqueous HCl solution and brine, dried (MgSO4) and concentrated. The resulting crude material (209 mg, 84%) was used without further purification.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed twice with 5% aqueous HCl solution and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting crude material (209 mg, 84%) was used without further purification

Sources & evidence

ORD record
ord-db1cb3330b1d4d89bcc51399715dfb30
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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