Lithium Hydroxide → HCID 118157551, compound

HRID 1779206Notes

Reaction equation

HRID 1779206 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:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[Li+].[OH-]>CO>[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:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[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

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90060203HCID 90060203, compound

Product 1

HCID 118157551HCID 118157551, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of No. 5233427, (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid (30 mg, 0.042 mmol) and methanol (4.0 mL) was added an aqueous solution (400 μL) of 2 M LiOH, and the mixture was stirred at room temperature. After confirming the consumption of the starting materials by LCMS, 1 M hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine and dried over anhydrous sodium sulfate. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by preparative HPLC and then freeze-dried to obtain the title compound (13.2 mg, 49%, white solid).

Workup

  1. additionTo a mixture of No
  2. customthe consumption of the starting materials by LCMS, 1 M hydrochloric acid
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe filtrate was then concentrated under reduced pressure
  8. customThe resulting residue was purified by preparative HPLC
  9. customfreeze-dried

Sources & evidence

ORD record
ord-e3ccfcb41397417f9097e2337ad47e86
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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