Sodium Hydroxide → HCID 58941300, compound

HRID 747628Notes

Reaction equation

HRID 747628 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)(=[O:17])=[O:16])[C@H:9]([C:11](OC)=[O:12])[CH3:10])=[C:4]([CH2:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:9]([CH3:10])[CH2:11][OH:12])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)(=[O:17])=[O:16])=[C:4]([CH2:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68566108HCID 68566108, compound

Product 1

HCID 58941300HCID 58941300, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1.1 g of methyl N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-N-[(3,4-dimethoxyphenyl)sulfonyl]alaninate in 15 ml of tetrahydrofuran are added, at room temperature, 158 mg of lithium aluminium hydride. After refluxing for 5 hours, the mixture is cooled to room temperature and hydrolysed with 15% sodium hydroxide solution. The medium is taken up in ethyl acetate and washed with water, the phases are separated by settling and the organic phase is dried over anhydrous sodium sulfate. The organic phase is concentrated and the residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) toluene/ethyl acetate mixture to give 0.215 g of the expected product.

Workup

  1. temperatureAfter refluxing for 5 hours
  2. washwashed with water
  3. customthe phases are separated
  4. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  5. concentrationThe organic phase is concentrated
  6. customthe residue is chromatographed on a column of silica gel
  7. washeluting with a 90/10 (v/v) toluene/ethyl acetate mixture

Sources & evidence

ORD record
ord-e14c6ebd086c41e9bad7a083ae390fac
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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