Lithium hydroxide, monohydrate → HCID 89415298, compound

HRID 2274533Notes

Reaction equation

HRID 2274533 reaction equation
[F:1][C:2]([F:39])([F:38])[C@H:3]([OH:37])[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[CH2:7][CH:6]1[C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30]([O:32]C)=[O:31].O.[OH-].[Li+]>CO.[Cl-].[NH4+]>[F:39][C:2]([F:1])([F:38])[C@H:3]([OH:37])[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[CH2:7][CH:6]1[C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30]([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89415289HCID 89415289, compound

Product 1

HCID 89415298HCID 89415298, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 3-{1-[(R)-3,3,3-trifluoro-2-hydroxypropyl]-4-[3-(trifluoromethoxy)benzyl]-1,2,3,4-tetrahydroquinoxalin-2-yl}benzoate (700 mg, 1.262 mmol) is made as described in Example 16 but with one stereochemical center unresolved. The compound was dissolved in MeOH (12.6 mL), lithium hydroxide monohydrate (530 mg, 12.62 mmol) was added, and the reaction mixture was heated to 60° C. for 4 hours. The crude mixture was dissolved in saturated ammonium chloride solution and extracted into EtOAc, the organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated, and purified on a silica gel column with a 0-100% Hex/EtOAc gradient. The major peak was concentrated to afford 3-{1-[(R)-3,3,3-trifluoro-2-hydroxypropyl]-4-[3-(trifluoromethoxy)benzyl]-1,2,3,4-tetra-hydroquinoxalin-2-yl}benzoic acid. MS m/z=541.09.

Workup

  1. extractionextracted into EtOAc
  2. dry with materialthe organic phase was dried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on a silica gel column with a 0-100% Hex/EtOAc gradient
  6. concentrationThe major peak was concentrated

Sources & evidence

ORD record
ord-353a65a00d254bda97ad9eb78cb2adb7
Source dataset
uspto-grants-2015_09
Patent number
US09126976B2

Reaction notes

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