Sodium Hydroxide → HCID 9910967, compound

HRID 1004082Notes

Reaction equation

HRID 1004082 reaction equation
C([O:3][C:4]([C:6]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH:14]=[C:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH:25]1[C:20]2[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[C:15](=[CH:14][CH2:13][CH2:12][N:9]3[CH2:8][CH2:7][C:6]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10895908HCID 10895908, compound

Product 1

HCID 9910967HCID 9910967, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

The above ester (4.75 g, 10.5 mmol) was dissolved in ethanol (40 ml) and 5 N sodium hydroxide (5 ml) was added. The mixture was stirred at 40° C. for 20 h, ethanol was evaporated in vacuo and water (50 ml) followed by acetic acid (4 ml) were added. The mixture was extracted with dichloromethane (100 ml), the organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The residue was crystallised from diethyl ether to give 2.2 g (45%) of the title compound as a solvate with water and acetic acid.

Workup

  1. customethanol was evaporated in vacuo and water (50 ml)
  2. additionwere added
  3. extractionThe mixture was extracted with dichloromethane (100 ml)
  4. dry with materialthe organic phase was dried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was crystallised from diethyl ether

Sources & evidence

ORD record
ord-eeff2739fe704edc9f0b54ed275048fb
Source dataset
uspto-grants-2000_04
Patent number
US06048856

Reaction notes

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