Methanol → HCID 66672865, compound

HRID 562622Notes

Reaction equation

HRID 562622 reaction equation
[CH3:1][C@@:2]1([CH2:8][CH2:9][C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)[CH2:6][O:5]C(=O)[NH:3]1.O1CCCC1.CO.[OH-].[K+]>O>[NH2:3][C@:2]([CH3:1])([CH2:8][CH2:9][C:10]1[N:11]([CH3:27])[CH:12]=[C:13]([C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:14]=1)[CH2:6][OH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 66673133HCID 66673133, compound

Product 1

HCID 66672865HCID 66672865, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (4R)-4-methyl-4-{2-[1-methyl-4-(5-phenylpentanoyl)pyrrol-2-yl]ethyl}-1,3-oxazolidin-2-one (11 mg, 0.03 mmol) obtained in Example (38a) in a mixed solvent of tetrahydrofuran (1 ml) and methanol (1 ml) was added a 5N aqueous potassium hydroxide solution (1 ml), and the resulting mixture was refluxed for 2 days. After cooling, water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo to afford the crude product of (2R)-2-amino-2-methyl-4-[1-methyl-4-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol (9 mg).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 days
  2. temperatureAfter cooling
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0c4d84057daa4532b38c269e47739016
Source dataset
uspto-grants-2011_11
Patent number
US08067396B2

Reaction notes

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