Sodium Hydroxide → HCID 86705556, compound

HRID 2279570Notes

Reaction equation

HRID 2279570 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:11][S:12][CH3:13])[CH:5]=[CH:6][C:7]=1[Cl:8].C1C=C(Cl)C=C(C(OO)=[O:30])C=1.[OH-:33].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:10][CH2:11][S:12]([CH3:13])(=[O:30])=[O:33])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86705555HCID 86705555, compound

Product 1

HCID 86705556HCID 86705556, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 372 (660 mg, 1.88 mmol) in DCM (20 mL) at 0° C. was added MCPBA (1393 mg, 5.65 mmol) and stirring was continued at RT for 24 h. A dilute solution of NaOH was added and the mixture was twice extracted with DCM, washed with brine, dried (MgSO4), and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with 10% EtOAc/hexane to afford 609 mg (84%) of (R)-tert-butyl 1-(3,4-dichlorophenyl)-3-(methylsulfonyl)propylcarbamate (374) as a white solid.

Workup

  1. extractionthe mixture was twice extracted with DCM
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-1eafedfb12c24459b09b5bd656476e9c
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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