Sodium Hydroxide → HCID 87735178, compound

HRID 902926Notes

Reaction equation

HRID 902926 reaction equation
C[O:2][C:3](=[O:37])[CH:4]([CH2:13][C:14](=[O:36])[NH:15][O:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+]>CO.O>[C:9]([O:8][C:6](=[O:7])[CH2:5][CH:4]([CH2:13][C:14](=[O:36])[NH:15][O:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]([OH:37])=[O:2])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 87735205HCID 87735205, compound

Product 1

HCID 87735178HCID 87735178, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the diester of example 62 (10.5 g, 20.8 mmol) in methanol (100 mL) was cooled in an ice bath and was treated drop wise with a solution of sodium hydroxide (1N, 42 mL). Stirring was continued for 30 minutes and then for an additional 48 hours at room temperature. The methanol was evaporated in a rotary evaporator and the alkaline reaction mixture was diluted with water followed by extracting with ether. The pH was adjusted to 4 by the addition of HCl (2N) and the acidic solution was extracted several times with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to give the desired product (10.2, 100%) as a white foam: 1H NMR (CDCl3, 400 MHz) 7.70 (d, 1H), 7.26-7.46 (m, 16H), 2.72-2.99 (m, 1H), 1.99-2.42 (m, 4H), 1.42 (s, 9H).

Workup

  1. waitfor an additional 48 hours at room temperature
  2. customThe methanol was evaporated in a rotary evaporator
  3. customthe alkaline reaction mixture
  4. extractionby extracting with ether
  5. additionThe pH was adjusted to 4 by the addition of HCl (2N)
  6. extractionthe acidic solution was extracted several times with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-6c91c4e84b2646f2b40d60ae4d4d319e
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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