Water → HCID 118046327, compound

HRID 596111Notes

Reaction equation

HRID 596111 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=C)[CH:5]=[C:6]([F:8])[CH:7]=1.I([O-])(=O)(=O)=[O:21].[Na+].[OH2:26]>C(Cl)(Cl)(Cl)Cl.C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:9]([NH:12][C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])[C:10]([OH:21])=[O:26])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 118054634HCID 118054634, compound

Product 1

HCID 118046327HCID 118046327, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-tert-butyl (1-(3-bromo-5-fluorophenyl)allyl)carbamate (1.235 g, 3.74 mmol) in CCl4 (4 mL), acetonitrile (4 mL) and water (6 mL) was treated with sodium periodate (1.680 g, 7.85 mmol) and RuCl3 (16 mg, 0.075 mmol). After 1 h, the reaction was complete. The reaction was partitioned between ethyl acetate and water. The organics were washed with brine, then filtered over celite and concentrated. The crude was redissolved in benzene, then filtered and concentrated again to provide crude (R)-2-(3-bromo-5-fluorophenyl)-2-((tert-butoxycarbonyl)amino)acetic acid (1.30 g, 99% yield) which was used directly. LCMS (m/z): 348.2 (MH+), 0.52 min.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organics were washed with brine
  3. filtrationfiltered over celite and
  4. concentrationconcentrated
  5. dissolutionThe crude was redissolved in benzene
  6. filtrationfiltered
  7. concentrationconcentrated again

Sources & evidence

ORD record
ord-b8b97d8bc91d4e0db619337ecef17292
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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