water acetonitrile CCl4 → HCID 86718352, compound

HRID 1518748Notes

Reaction equation

HRID 1518748 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]([C:15]1[O:16]C=CC=1)[C@@H:10]([CH3:14])[CH2:11][O:12][CH3:13])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH2:21].C(Cl)(Cl)(Cl)Cl.CC#N>CC#N.O>[C:1]([O:5][C:6]([N:7]([CH3:8])[C@@H:9]([C@@H:10]([CH3:14])[CH2:11][O:12][CH3:13])[C:15]([OH:16])=[O:21])=[O:20])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 22592919water acetonitrile CCl4HCID 86718353HCID 86718353, compound

Product 1

HCID 86718352HCID 86718352, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of NalO4 (969.0 mg, 4.5 mmol, 6.0 equiv) in H2O/CCl4/CH3CN (3/2/3, 21 mL) was added RuCl3 (53.0 mg, 0.26 mmol, 0.34 equiv). After stirring for 15 minutes, a solution of ((1S,2R)-1-furan-2-yl-3-methoxy-2-methyl-propyl methylcarbamic acid tert-butyl ester (214.0 mg, 0.76 mmol) in CH3CN (4 mL) was added. After 15 minutes, the mixture was diluted with water (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed successively with saturated aqueous NaHSO3, brine, dried over Na2SO4, and concentrated in vacuo to give (2S,3R)-2-(tertbutoxycarbonyl-methyl-amino)-4-methoxy-3-methyl-butyric acid (180.0 mg).

Workup

  1. waitAfter 15 minutes
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic layers were washed successively with saturated aqueous NaHSO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-815fdd9a511f4d17a5b5dae5e6630404
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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