Hydrochloric Acid → HCID 67271011, compound

HRID 602483Notes

Reaction equation

HRID 602483 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([NH:15][C@@H:16]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:18]([CH2:28][C:29]([O:31]C)=[O:30])[CH2:17]2)=[O:14])=[N:5]1)([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:24]([O:23][C:21]([N:19]1[CH2:20][C@@H:16]([NH:15][C:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)=[O:14])[CH2:17][C@H:18]1[CH2:28][C:29]([OH:31])=[O:30])=[O:22])([CH3:25])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67270240HCID 67270240, compound

Product 1

HCID 67271011HCID 67271011, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl (2S,4S)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate (0.65 g, 1.46 mmol, step 5 of Example 9) in methanol (10 mL) was added 2N sodium hydroxide aqueous solution (10 mL) at room temperature and the mixture was stirred for 2.5 h. The resulting solution was acidified with 2N hydrochloric acid to be pH 3. Then the mixture was extracted with dichloromethane (10 mL×3). The organic layer was dried over sodium sulfate and concentrated to give 0.62 g (98%) of the title compound as a colorless oil. The residue was used for the next step without further purification.

Workup

  1. extractionThen the mixture was extracted with dichloromethane (10 mL×3)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d4388476de9640eb8e70ff623f517208
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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