Methanol → HCID 68736379, compound

HRID 1511457Notes

Reaction equation

HRID 1511457 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[N:14]=[C:13]([N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)[CH:12]=2)[CH2:7][N:6]1[C:28](=[O:42])[C@@H:29]([NH:34][C:35]([NH:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:4].[CH3:43]O.[OH-].[Na+]>O1CCCC1>[CH3:43][C@@:5]1([C:3]([OH:2])=[O:4])[CH2:9][C@@H:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[N:14]=[C:13]([N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)[CH:12]=2)[CH2:7][N:6]1[C:28](=[O:42])[C@@H:29]([NH:34][C:35]([NH:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])[C:30]([CH3:32])([CH3:31])[CH3:33]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57818328HCID 57818328, compound

Product 1

HCID 68736379HCID 68736379, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-methyl-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)-pyrrolidine-2-carboxylate was treated with methanol (6.0 mL), tetrahydrofuran (3.0 mL) and 1N sodium hydroxide (6. mL). After 1 hour at room temperature, the reaction mixture was concentrated, acidified with 1N HCl and extracted with ethyl acetate. The combined ethyl acetate layers were then washed with brine and dried (MgSO4). The ethyl acetate layer was then filtered and evaporated to dryness to give (2S,4R)-methyl-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-4-(7-methoxy-2-(1H-pyrazol-1-yl)quinolin-4-yloxy)-pyrrolidine-2-carboxylic acid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were then washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe ethyl acetate layer was then filtered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-68cf2efda334405584a6f7d73f714253
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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