Methanol → HCID 10253045, compound

HRID 845901Notes

Reaction equation

HRID 845901 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:16])[C:3]=1[CH2:17][C:18]1([CH3:40])[C:22](=[O:23])[O:21]C(C2C=CC=CC=2)[N:19]1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].CO.[OH-].[Na+]>C(Cl)Cl>[CH3:40][C:18]([NH:19][C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])([CH2:17][C:3]1[C:4]([CH3:16])=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][C:2]=1[CH3:1])[C:22]([OH:23])=[O:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 10324866HCID 10324866, compound

Product 1

HCID 10253045HCID 10253045, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound of Example 54 (2.42 g) was dissolved in 5 ml of 1:1 CH2Cl2 : methanol, and added to methanolic NaOH (1N, 100 ml). After 3 hr of stirring, the mixture was concentrated to 75 ml, diluted to 500 ml with water, and extracted twice with ether to remove non-acidic contaminants. The aqueous phase was made acidic with 0.5N KHSO4, and then extracted four times with CH2Cl2. The CH2Cl2 fractions were combined, dried (MgSO4), filtered, and stripped to give the title compound (1.75 g). NMR:α methyl group at ∫2.75.

Workup

  1. concentrationthe mixture was concentrated to 75 ml
  2. additiondiluted to 500 ml with water
  3. extractionextracted twice with ether
  4. customto remove non-acidic contaminants
  5. extractionextracted four times with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-916b1833d3214d4aa4819bf44fbc6cc7
Source dataset
uspto-grants-1988_07
Patent number
US04760180

Reaction notes

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