Pyridine → HCID 57947605, compound

HRID 409842Notes

Reaction equation

HRID 409842 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-c7aa689fe18f4d3895ce2d69e2df989d
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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