Pyridine → HCID 23405697, compound

HRID 489030Notes

Reaction equation

HRID 489030 reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[CH2:7]([O:14][C:15]([NH:17][C@H:18]([C:22]([O:24][CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28])=[O:23])[CH:19]([CH3:21])[CH3:20])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1>C(Cl)Cl>[C:2](=[O:3])([O:4][CH2:5][Cl:6])[O:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][O:24][C:22](=[O:23])[C@H:18]([CH:19]([CH3:21])[CH3:20])[NH:17][C:15]([O:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 23387528HCID 23387528, compound

Product 1

HCID 23405697HCID 23405697, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloromethyl chloroformate (1.50 mL, 16.6 mmol) was added to a solution of the alcohol (2.74 g, 8.12 mmol) from step (a) and pyridine (4.9 mL, 61 mmol) in 40 mL dry CH2Cl2, in an ice bath. After stirring for 1 h, the mixture was diluted with CH2Cl2 and washed successively with water, saturated NaHCO3, and brine. The organic phase was dried over anhydrous Na2SO4 and concentrated, coevaporating several times with toluene on a rotavapor. Flash column chromatography (silica, 2/1 petroleum ether-ethyl acetate) gave 3.31 g (95%) of the title compound.

Workup

  1. washwashed successively with water, saturated NaHCO3, and brine
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6954c0991c294fd18ceef4054c98ad6c
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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