Pyridine → HCID 11207432, compound

HRID 1261436Notes

Reaction equation

HRID 1261436 reaction equation
[CH2:1]([C:3]([CH2:15][OH:16])([CH3:14])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[OH:2].N1C=CC=CC=1.[C:23](=O)=[O:24].CC(C)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH3:14][C:3]1([C:4]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH2:15][O:16][C:23](=[O:24])[O:2][CH2:1]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 94429TriphosgeneHCID 11287527Phenylmethyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoateHCID 18522661Acetone cardice

Product 1

HCID 11207432HCID 11207432, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzyl 2,2-bis(methylol)propionate (BnMPA) (11.2 g, 0.05 mol) was dissolved in CH2Cl2 (150 mL) and pyridine (25 mL, 0.3 mol) and the solution was chilled to −75° C. with dry ice/acetone under N2 atmosphere. A solution of triphosgene (7.5 g, 25 mmol) in CH2Cl2 (150 mL) was added dropwise over 1 hours, and then the reaction mixture was allowed to warm to room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl (75 mL), after which the organic layer was washed with 1 M aqueous HCl (3×100 mL), saturated aqueous NaHCO3 (1×100 mL), dried over MgSO4, filtered and evaporated. The resulting solid was recrystallized from ethyl acetate (15 mL) to give MTCOBn as a white solid (10.7 g, 86%). 1H NMR (400 MHz, CDCl3, 22° C.): delta 7.37 (m, 5H, PhH), 5.20 (s, 2H, —OCH2Ph), 4.69 (d, 2H, —CH2OCOO), 4.23 (d, 2H, —CH2OCOO), 1.31 (s, 3H, —CH3).

Workup

  1. customThe reaction was quenched by addition of saturated aqueous NH4Cl (75 mL)
  2. washafter which the organic layer was washed with 1 M aqueous HCl (3×100 mL), saturated aqueous NaHCO3 (1×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting solid was recrystallized from ethyl acetate (15 mL)

Sources & evidence

ORD record
ord-0cd0b60ac68d4a71b2c0fe596596f22c
Source dataset
uspto-grants-2013_06
Patent number
US08470891B2

Reaction notes

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