Sodium → HCID 10445008, compound

HRID 1614683Notes

Reaction equation

HRID 1614683 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH:7](C(C2C=CC(C)=CC=2)=O)[OH:8])[O:5][C@@H:4]([N:18]2[CH:25]=[C:24]([C:26]#[C:27][Si](C)(C)C)[C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:3]1.[Na]>C[O-].[Na+].CO>[C:26]([C:24]1[C:22](=[O:23])[NH:21][C:19](=[O:20])[N:18]([CH:25]=1)[C@@H:4]1[O:5][C@H:6]([CH2:7][OH:8])[C@@H:2]([F:1])[CH2:3]1)#[CH:27]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 67859441HCID 67859441, compound

Product 1

HCID 10445008HCID 10445008, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10942334Sodium MethoxideSolvent

Procedure

A solution of the product of Stage c), in 0.2M sodium methoxide in methanol (freshly prepared from sodium and methanol) is stirred at room temperature for 3.0 hr. then neutralized by portionwise addition of Dowex 50 (H+) ion exchange resin. The resin is filtered off and washed well with methanol. The filtrate is evaporated to dryness and the residue partitioned between water and ether. The aqueous layer is washed with ether then evaporated to dryness, the residue triturated with ethanol and the solid filtered and washed with ether to give the title compound.

Workup

  1. additionthen neutralized by portionwise addition of Dowex 50 (H+) ion exchange resin
  2. filtrationThe resin is filtered off
  3. washwashed well with methanol
  4. customThe filtrate is evaporated to dryness
  5. customthe residue partitioned between water and ether
  6. washThe aqueous layer is washed with ether
  7. customthen evaporated to dryness
  8. customthe residue triturated with ethanol
  9. filtrationthe solid filtered
  10. washwashed with ether

Sources & evidence

ORD record
ord-2a1ebe5a5a4a4270908b37069fd1729d
Source dataset
uspto-grants-1993_03
Patent number
US05198539

Reaction notes

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