Sodium Hydroxide → HCID 11718065, compound

HRID 229374Notes

Reaction equation

HRID 229374 reaction equation
C(=O)([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22]([F:25])[CH:23]=3)[N:18]3[CH:27]=[CH:28][CH:29]=[C:17]3[CH:16]2[CH2:30][CH3:31])(=[O:14])=[O:13])=[CH:8][CH:7]=1)OCC.[OH-].[Na+]>CO>[CH2:30]([CH:16]1[N:15]([S:12]([C:9]2[CH:8]=[CH:7][C:6]([OH:5])=[CH:11][CH:10]=2)(=[O:14])=[O:13])[C:24]2[C:19](=[CH:20][C:21]([F:26])=[C:22]([F:25])[CH:23]=2)[N:18]2[CH:27]=[CH:28][CH:29]=[C:17]12)[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69062853HCID 69062853, compound

Product 1

HCID 11718065HCID 11718065, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 50 ml round bottom flask charged with 30 ml of methanol was added 0.67 g (1.4 mmol) of the product from Example 6, then 2 ml of 2N NaOH. The solution was stirred for 0.5 hr to completion then concentrated. The residue was neutralized with 2N HCl and extracted with ethyl acetate (2×10 ml), dried (MgSO4) and concentrated. The solid was passed through a plug of silica gel eluting with 40% ethyl acetate:hexane. The product so obtained was triturated with hexane to induce solidification, then crystallized from ethyl acetate:hexane to afford 0.47 g (86%) of product as colorless crystals, mp 177-179° C.

Workup

  1. concentrationthen concentrated
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe product so obtained
  6. customwas triturated with hexane
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9a37b2bf25ba448f9bb2b05d46f25b81
Source dataset
uspto-grants-2009_07
Patent number
US07563793B2

Reaction notes

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