Chloroform → HCID 19080375, compound

HRID 865524Notes

Reaction equation

HRID 865524 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:40])[CH:15]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[CH:19][C:18]=2[CH2:27][CH:28]([CH3:30])[CH3:29])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+].C(Cl)(Cl)Cl>CO>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14](=[O:40])[CH:15]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][C:18]=2[CH2:27][CH:28]([CH3:30])[CH3:29])(=[O:11])=[O:12])=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 19080379HCID 19080379, compound

Product 1

HCID 19080375HCID 19080375, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 0.294 g (0.52 mmol) of the product of Example 60 dissolved in 3.0 mL of methanol was added 1.0 mL of a 5.0 N aqueous solution of sodium hydroxide. The reaction mixture was magnetically stirred at 60° C. After 3 hours TLC analysis (CHCl3 --MeOH--NH4OH80:15:1) indicated complete hydrolysis of the ester. The reaction was cooled to room temperature, adjusted to pH=5 with dropwise addition of 1.0 N HCI, then partitioned between EtOAc and water. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and evaporated. The residue was dried in vacuo to afford 0.238 g (83%) of the title compound as an amorphous powder.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionadjusted to pH=5 with dropwise addition of 1.0 N HCI
  3. custompartitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-5719b88301e1437eb6beb026d4566f2e
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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