Lithium Hydroxide → HCID 118157506, compound

HRID 1779199Notes

Reaction equation

HRID 1779199 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][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C@:22]([CH2:27][C:28]#[N:29])([OH:26])[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:30]=[CH:31]/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C@:22]([CH2:27][C:28]#[N:29])([OH:26])[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 90060347HCID 90060347, compound

Product 1

HCID 118157506HCID 118157506, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

No. 5250270, (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-cyanomethyl-2-hydroxy-12-oxo-nonadec-4-enoic acid (81 mg, 0.127 mmol) was dissolved in methanol (4.0 mL), and 2 M LiOH (0.40 mL) was added. 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 resulting organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure. The resulting residue was purified by preparative HPLC and freeze-dried to obtain the title compound (11 mg, 14% yield, yellow oil).

Workup

  1. customthe consumption of the starting materials by LCMS, 1 M hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe resulting organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by preparative HPLC
  8. customfreeze-dried

Sources & evidence

ORD record
ord-dd863de45f2340dba1507f28ddca2b4c
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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