Water → HCID 88140200, compound

HRID 975238Notes

Reaction equation

HRID 975238 reaction equation
[ClH:1].C([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][CH2:14][O:15]/[N:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH2:8]1)=[O:6])C.O>C(O)C.[OH-].[Na+]>[ClH:1].[CH3:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1/[CH:17]=[N:16]/[O:15][CH2:14][CH2:13][N:9]1[CH2:10][CH2:11][CH2:12][C@@H:7]([C:5]([OH:6])=[O:4])[CH2:8]1

Participants

5

Reactant 2

HCID 962WaterHCID 88378163HCID 88378163, compound

Product 1

HCID 88140200HCID 88140200, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The above ester (2.22 g, 6.3 mmol) was dissolved in a mixture of ethanol (65 ml) and 12N sodium hydroxide (4.9 ml) and stirred at ambient temperature for 1 h. Water (20 ml) was added and the mixture extracted with diethyl ether (3×30 ml). The phases were separated and pH in the aqueous phase was adjusted to 5 with 2N hydrochloric acid. The aqueous phase was extracted with dichloromethane (2×40 ml) and the solvent was evaporated from the combined organic phases in vacuo. The residue was dissolved in toluene (25 ml), then methanol (0.17 ml) and chlorotrimethylsilane (0.52 ml) were added and the mixture left for crystallisation. This afforded 0.51 g of the title compound as a solid. M.p. 108.5°-109.9° C.

Workup

  1. extractionthe mixture extracted with diethyl ether (3×30 ml)
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (2×40 ml)
  4. customthe solvent was evaporated from the combined organic phases in vacuo
  5. dissolutionThe residue was dissolved in toluene (25 ml)
  6. additionmethanol (0.17 ml) and chlorotrimethylsilane (0.52 ml) were added
  7. waitthe mixture left for crystallisation

Sources & evidence

ORD record
ord-30302ca13c2a4c84ba5d902705ec8a87
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

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