Methanol → HCID 118157463, compound

HRID 1779213Notes

Reaction equation

HRID 1779213 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:30]=[CH:31]/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]([OH:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C@@:22]([OH:29])([CH2:26][CH2:27][OH:28])[C:23]([O-:25])=[O:24])=[O:20])[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[K+].CO.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:30]=[CH:31]/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]([OH:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C@@:22]([OH:29])([CH2:26][CH2:27][OH:28])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 131734863HCID 131734863, compound

Product 1

HCID 118157463HCID 118157463, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of No. 5286993, potassium (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2,12-dihydroxy-2-(2-hydroxy-ethyl)-nonadec-4-enoate (40 mg, 0.0584 mmol) and methanol (2.0 mL) were added water (2.0 mL) and potassium carbonate (40 mg, 0.146 mmol), and the mixture was stirred at room temperature for 4 hours. After confirming the consumption of the starting materials by LCMS, water was added and the mixture was extracted with ethyl acetate. To the aqueous layer was then added 1 M hydrochloric acid until pH 7 was reached. The organic layer was washed with a saturated brine, and dried over anhydrous sodium sulfate. The filtrate was then concentrated under reduced pressure to obtain the title compound (15 mg, 41% yield, white solid).

Workup

  1. additionTo a mixture of No
  2. customthe consumption of the starting materials by LCMS, water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. additionTo the aqueous layer was then added 1 M hydrochloric acid until pH 7
  6. washThe organic layer was washed with a saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-ebff68d74895490681ad638b9e9a93b1
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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