Pivaloyl chloride → HCID 68935884, compound
Reaction equation
[OH:1][CH2:2][C@@H:3]([C@@H:5]1[C@:13]2([CH3:14])[C@H:8]([C@@H:9]([OH:15])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)[CH3:4].[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>ClCCl.N1C=CC=CC=1>[C:16]([O:1][CH2:2][C@@H:3]([C@@H:5]1[C@:13]2([CH3:14])[C@H:8]([C@@H:9]([OH:15])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)[CH3:4])(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
The compound of Example 3D (0.58 g, 2.7 mmol) was dissolved in 4 mL of dichloromethane and 2 mL of pyridine; the solution was cooled to 0° C., and 0.39 mL of pivaloyl chloride was added dropwise over 5 minutes. The resultant mixture was stirred at 0° C. for 2.5 hours, then it was quenched with water, and the mixture was concentrated in vacuo with the bath maintained below ambient temperature. The crude material was partitioned between ether and 0.5 N aqueous HCl; the organic phase was washed with 0.5 N aqueous HCl, then brine, and dried over Na2SO4. The solvents were removed in vacuo; the residue (0.96 g) was carried forward without further purification.
Workup
- customit was quenched with water
- concentrationthe mixture was concentrated in vacuo with the bath
- temperaturemaintained below ambient temperature
- customThe crude material was partitioned between ether and 0.5 N aqueous HCl
- washthe organic phase was washed with 0.5 N aqueous HCl
- dry with materialbrine, and dried over Na2SO4
- customThe solvents were removed in vacuo
- customthe residue (0.96 g) was carried forward without further purification
Sources & evidence
- ORD record
- ord-1229955455384c7a8b069a1bc78322ba
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377913B2
Reaction notes
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