Sodium Hydroxide → HCID 67915650, compound

HRID 1681154Notes

Reaction equation

HRID 1681154 reaction equation
[CH3:1][C:2]([CH3:40])([O:4][C:5]([NH:7][C@@H:8]([C:32]([NH:34][CH2:35][C:36]([O:38]C)=[O:37])=[O:33])[C:9]([S:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:11])[CH3:10])=[O:6])[CH3:3].[OH-].[Na+].OS([O-])(=O)=O.[K+]>CO>[CH3:3][C:2]([CH3:40])([O:4][C:5]([NH:7][C@@H:8]([C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])[C:9]([S:12][C:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:10])[CH3:11])=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 131717668HCID 131717668, compound

Product 1

HCID 67915650HCID 67915650, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a MeOH (160 mL) solution of the product of Example 32 (22.2 g, 0.039 mol) was added dropwise to vigorously-stirred 80 mL of 1.0 N NaOH. After 2 hours, the pH of the homogenous solution was adjusted to pH 2 with 1.0 M KHSO4. The white precipitate generated was filtered, washed with water, dried in the vacuum oven at 50° C. over night and dissolved in 150 mL of CH2Cl2. This solution was filtered before the solvent volume was reduced by rotary evaporation, and the product precipitated with n-hexane. The white solid product was filtered, washed with hexane, and dried in vacuo. A crude 24.8 g (98% by HPLC) sample of the desired title material was isolated as a white solid, and was used without further purification.

Workup

  1. filtrationThe white precipitate generated was filtered
  2. washwashed with water
  3. customdried in the vacuum oven at 50° C. over night
  4. dissolutiondissolved in 150 mL of CH2Cl2
  5. filtrationThis solution was filtered before the solvent volume
  6. customwas reduced by rotary evaporation
  7. customthe product precipitated with n-hexane
  8. filtrationThe white solid product was filtered
  9. washwashed with hexane
  10. customdried in vacuo

Sources & evidence

ORD record
ord-ffcf8c8714504b5f9bc0f69cfdf84881
Source dataset
uspto-grants-1992_12
Patent number
US05169833

Reaction notes

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