Triacetoxyperiodinane → HCID 86705541, compound

HRID 2279553Notes

Reaction equation

HRID 2279553 reaction equation
[Cl: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])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S(=O)(O)[O-].[Na+]>CCOCC.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH:10]=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 23665763Sodium BisulfiteHCID 86705509HCID 86705509, compound

Product 1

HCID 86705541HCID 86705541, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 326 (1.134 g, 3.914 mmol) and DCM (8 mL) under nitrogen cooled to 0° C. was added NaHCO3 (0.9864 g, 11.74 mmol) followed by Dess-Martin periodinane (2.490 g, 5.871 mmol) both as solids. After 3 h, the reaction was about 50% complete by TLC. The reaction was warmed to RT for 1 h, then the reaction was diluted with Et2O (10 mL) and poured into ice cold satd. aq. NaHCO3 (50 mL) containing sodium bisulfite (15 gm). After stirring for 15 min, the layers were separated and the aqueous phase was extracted with Et2O (2×30 mL). The combined organic extracts were washed sequentially with satd. aq. NaHCO3 (2×50 mL) and brine (1×50 mL), dried (MgSO4), filtered and concentrated to afford 0.814 g (72%) of (S)-tert-butyl 1-(3-chloro-4-fluorophenyl)-2-oxoethylcarbamate (328) as a yellow foam.

Workup

  1. additionpoured into ice cold satd
  2. customthe layers were separated
  3. extractionthe aqueous phase was extracted with Et2O (2×30 mL)
  4. washThe combined organic extracts were washed sequentially with satd
  5. dry with materialaq. NaHCO3 (2×50 mL) and brine (1×50 mL), dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10371d1527554b1a90748e8f6451c78d
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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