Lithium Hydroxide → HCID 117942124, compound

HRID 1499186Notes

Reaction equation

HRID 1499186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([O:13][C:14]2[N:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[N:17]=[C:16]([N:24]3[CH2:48][CH2:47][C:27]4([CH2:31][N:30]([C:32]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[O:33])[CH:29]([C:42]([O:44]CC)=[O:43])[CH2:28]4)[CH2:26][CH2:25]3)[CH:15]=2)[C:9]([F:12])([F:11])[F:10])=[C:4]([N:49]2[CH:53]=[CH:52][C:51]([CH3:54])=[N:50]2)[CH:3]=1.C1COCC1.[Li+].[OH-]>O>[CH2:35]([O:34][C:32]([N:30]1[CH:29]([C:42]([OH:44])=[O:43])[CH2:28][C:27]2([CH2:26][CH2:25][N:24]([C:16]3[CH:15]=[C:14]([O:13][C@H:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[N:49]4[CH:53]=[CH:52][C:51]([CH3:54])=[N:50]4)[C:9]([F:10])([F:11])[F:12])[N:19]=[C:18]([S:20]([CH3:23])(=[O:21])=[O:22])[N:17]=3)[CH2:48][CH2:47]2)[CH2:31]1)=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 8028TetrahydrofuranHCID 117947770HCID 117947770, compound

Product 1

HCID 117942124HCID 117942124, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-benzyl 3-ethyl 8-(6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)-2-(methylsulfonyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (2.10 g, 2.65 mmol) in 2:1 THF:H2O (90 mL) was added LiOH (127 mg, 5.3 mmol), and the reaction was stirred at RT for 21 h, after which additional LiOH (65 mg, 2.6 mmol) was added, and the reaction was stirred for 8 h longer. The reaction was then quenched with 1 N HCl to pH<1, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide 2-((benzyloxy)carbonyl)-8-(6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)-2-(methylsulfonyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid as an off-white solid which was used directly without further purification.

Workup

  1. stirringthe reaction was stirred for 8 h longer
  2. customThe reaction was then quenched with 1 N HCl to pH<1
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80940ebbc8a04519ac300276945af533
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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