Methanol → HCID 118157636, compound

HRID 1779210Notes

Reaction equation

HRID 1779210 reaction equation
C([O:4][CH2:5][CH2:6][C@:7]([OH:50])([C@@H:11]([C:29](=[O:49])[NH:30][C@H:31]([CH2:44][O:45]C(=O)C)[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]#[C:42][CH3:43])=[CH:35][CH:34]=1)/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:8]([OH:10])=[O:9])(=O)C.CO.[Li+].[OH-]>O>[CH2:40]([O:39][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][C@H:31]([NH:30][C:29]([C@@H:11](/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@@:7]([OH:50])([CH2:6][CH2:5][OH:4])[C:8]([OH:10])=[O:9])=[O:49])[CH2:44][OH:45])=[CH:38][CH:37]=1)[C:41]#[C:42][CH3:43]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 118157381HCID 118157381, compound

Product 1

HCID 118157636HCID 118157636, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of No. 5257015 , (E)-(2S,3S)-2-(2-acetoxy-ethyl)-3-[(S)-1-acetoxymethyl-2-(4-but-2-ynyloxy-phenyl)-ethylcarbamoyl]-2-hydroxy-12-oxo-nonadec-4-enoic acid (17 mg, 0.0244 mmol) and methanol (1.7 mL) were added water (49 μL) and LiOH (2.4 mg, 0.0983 mmol), and the mixture was stirred at room temperature. After confirming the consumption of the starting materials by LCMS, the reaction solution was purified directly by preparative HPLC, and freeze-dried to obtain the title compound (9 mg, 60% yield, yellow oil).

Workup

  1. additionTo a mixture of No
  2. customthe consumption of the starting materials by LCMS
  3. customthe reaction solution was purified directly by preparative HPLC
  4. customfreeze-dried

Sources & evidence

ORD record
ord-80fb535600434479aa5e108370e56e47
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…