Pyridine → HCID 57947605, compound

HRID 416414Notes

Reaction equation

HRID 416414 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33]>C1COCC1>[C:32]([O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][C@H:10]([N:17]([C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[CH3:25])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 57947943HCID 57947943, compound

Product 1

HCID 57947605HCID 57947605, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-5-hydroxy-4,4-dimethylpentan-2-yl(methyl)carbamate (1.23 g, 3.27 mmol) in THF (20 mL) were added pyridine (0.79 mL) and acetyl chloride (0.386 g, 4.91 mmol). The reaction mixture was stirred at RT overnight and filtered. The filtrate was concentrated to give (S)-4-(tert-butoxycarbonyl(methyl)amino)-5-(tert-butyldimethylsilyloxy)-2,2-dimethylpentyl acetate (1.36 g, crude), which was used without further purification. LRMS (M-Boc+H+) m/z 318.2

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c4c82f7e909a4e1780d423b41fac3b3c
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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