Methanol → HCID 9998635, compound

HRID 1180451Notes

Reaction equation

HRID 1180451 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:31])[C@@H:6]([O:11][C@H:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].CO>C1COCC1.CC(O)=O.[Na]>[C:1]([CH2:3][NH:4][C:5](=[O:31])[C@@H:6]([O:11][C@@H:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

Participants

6

Reactant 2

HCID 887MethanolHCID 10342788HCID 10342788, compound

Product 1

HCID 9998635HCID 9998635, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolventHCID 5360545SodiumSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2S)-N-(cyanomethyl)-4-methyl-2-[((R)-phenyl{4-[(trimethylsilyl)ethynyl]phenyl}methyl)oxy]pentanamide from example 70 (0.12 mmol, 50 mg) in THF:MeOH (1.3 mL: 50 uL) at 0° C., AcOH (3 drops) was added followed by tetrabutylammonium triphenyldifluorosilicate (0.01 mmol, 7 mg). The mixture was stirred 20 minutes at 0° C. The mixture was diluted with 1% sodium hydroxyde (3 mL) and diethlyl ether (5 mL). The phases were separated. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification: 30:70 (AcOEt:Hex.) gave the title amide.

Workup

  1. customThe phases were separated
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customPurification

Sources & evidence

ORD record
ord-05c6d29228b84589bd9d3459f96cf058
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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