Chloromethyl pivalate → HCID 131724776, compound

HRID 983514Notes

Reaction equation

HRID 983514 reaction equation
OC[CH2:3][C@@:4]12[C@@H:15]3[CH2:16][C@@:11]([CH:23]=[O:24])([C@:12]1([C:20]([OH:22])=[O:21])[C:13]([CH:17]([CH3:19])[CH3:18])=[CH:14]3)[CH:10]1[CH:6]([CH:7]([CH3:26])[CH:8]([Cl:25])[CH2:9]1)[CH2:5]2.C([O-])(O)=[O:28].[Na+].Cl[CH2:33][O:34][C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])=[O:36]>CN(C=O)C>[Cl:25][CH:8]1[CH:7]([CH3:26])[CH:6]2[CH:5]([C@@:4]3([CH:3]=[O:28])[CH2:15][C@H:16]4[C@@:11]([CH2:23][OH:24])([CH2:10]2)[C@:12]3([C:20]([O:22][CH2:33][O:34][C:35](=[O:36])[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:21])[C:13]([CH:17]([CH3:19])[CH3:18])=[CH:14]4)[CH2:9]1

Participants

5

Reactant 3

HCID 87885Chloromethyl pivalateHCID 516892Sodium BicarbonateHCID 86594184HCID 86594184, compound

Product 1

HCID 131724776HCID 131724776, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 41 (23.7 mg) in DMF (5 mL) was added NaHCO3 (109 mg, 1.30 mmol), followed by ClCH2OC(O)CMe3 (0.093 mL, 0.65 mmol). The mixture was stirred at room temperature overnight. After aqueous work-up (ether) and purification by a PTLC, about 26.2 mg of 42 was obtained.

Workup

  1. customAfter aqueous work-up (ether) and purification by a PTLC

Sources & evidence

ORD record
ord-9e974ff238c14e9da6de8a983f900511
Source dataset
uspto-grants-2005_03
Patent number
US06864278B2

Reaction notes

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