Lithium hydroxide, monohydrate → HCID 86706091, compound

HRID 2176252Notes

Reaction equation

HRID 2176252 reaction equation
C[O:2][C:3]([C:5]1(/[CH:11]=[CH:12]/[C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19]([C@H:23]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:24])=[N:20]3)=[CH:15][CH:14]=2)[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)=[O:4].O.[OH-].[Li+]>O1CCCC1.O>[C:29]([O:28][C:26]([NH:25][C@@H:23]([C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][C:13](/[CH:12]=[CH:11]/[C:5]3([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7][O:6]3)=[CH:14][CH:15]=2)[N:20]=1)[CH3:24])=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86706090HCID 86706090, compound

Product 1

HCID 86706091HCID 86706091, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{(E)-2-[2-((R)-1-tert-butoxycarbonylamino-ethyl)-quinolin-7-yl]-vinyl}-tetrahydro-pyran-2-carboxylic acid methyl ester (130 mg, 0.3 mmol) in tetrahydrofuran (6 mL) was stirred at 5° C. under nitrogen. A solution of lithium hydroxide monohydrate (25 mg, 0.6 mmol) in water (1.5 mL) was added and the reaction mixture was stirred at room temperature for 18 h. The majority of the organic solvent was evaporated. The solution was acidified to pH 2 with ice-cold hydrochloric acid (2 M) and the mixture was extracted with dichloromethane. The organic extracts were combined and washed with brine. The organic solution was filtered through a hydrophobic frit and the filtrate was evaporated to afford 2-{(E)-2-[2-((R)-1-tert-butoxycarbonylamino-ethyl)-quinolin-7-yl]-vinyl}-tetrahydro-pyran-2-carboxylic acid (135 mg, 0.3 mmol) as a yellow gum which was used crude in the next step. LCMS (m/z) 427.1 [M+H], Tr=2.17 min.

Workup

  1. customThe majority of the organic solvent was evaporated
  2. extractionthe mixture was extracted with dichloromethane
  3. washwashed with brine
  4. filtrationThe organic solution was filtered through a hydrophobic frit
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1ac23813be13495eb47ee9f47567f749
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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