Lithium Hydroxide → HCID 71468591, compound

HRID 1401078Notes

Reaction equation

HRID 1401078 reaction equation
[CH:1]([N:4]([C:20](=[O:39])/[CH:21]=[CH:22]/[C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:24]=1)[NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]([O:17]C)=[O:16])[CH:8]=1)([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:35]([O:34][C:32]([N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](/[CH:22]=[CH:21]/[C:20]([N:4]([CH:1]([CH3:3])[CH3:2])[NH:5][C:6]([C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[O:13][CH2:14][C:15]([OH:17])=[O:16])=[O:19])=[O:39])=[CH:24]1)=[O:33])([CH3:37])([CH3:38])[CH3:36]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71468458HCID 71468458, compound

Product 1

HCID 71468591HCID 71468591, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

(E)-tert-butyl 3-(3-(1-isopropyl-2-(3-(2-methoxy-2-oxoethoxy)benzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (70 mg, 0.13 mmol) was dissolved in THF/H2O (2 ml/1 ml), stirred for 20 min, lithiumhydroxide (10.96 mg, 0.26 mmol) was slowly drop-wise added, and stirred at room temperature for 12 hr. THF was concentrated under reduced pressure, and after titration with 6N HCl at pH=2, the reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4 filtered, and concentrated under reduced pressure so that while solid form of (E)-2-(3-(2-(3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acryloyl)-2-isopropylhydrazinecarbonyl)phenoxy)acetic acid was obtained (68.1 mg, 99%).

Workup

  1. stirringstirred at room temperature for 12 hr
  2. concentrationTHF was concentrated under reduced pressure
  3. additionafter titration with 6N HCl at pH=2, the reaction mixture was diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure so that while solid form of (E)-2-(3-(2-(3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acryloyl)-2-isopropylhydrazinecarbonyl)phenoxy)acetic acid
  8. customwas obtained (68.1 mg, 99%)

Sources & evidence

ORD record
ord-877176f86a5245ceb8fe947c2c5ea8ed
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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