Water → 2-Benzyloxycarbonylamino-3-(2-methoxy-pyrimidin-5-yl)-acrylic acid methyl ester

HRID 2250220Notes

Reaction equation

HRID 2250220 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][N:10]=1.[C:17]([O:20][CH2:21]C)(=[O:19])[CH3:18].[OH2:23]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:21][O:20][C:17](=[O:19])[C:18]([NH:10][C:9]([O:8][CH2:1][C:2]1[CH:5]=[CH:13][CH:12]=[CH:11][CH:3]=1)=[O:23])=[CH:15][C:12]1[CH:13]=[N:14][C:9]([O:8][CH3:7])=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31518662-Methoxypyrimidine-5-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 687058772-Benzyloxycarbonylamino-3-(2-methoxy-pyrimidin-5-yl)-acrylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of potassium t-butoxide (1.23 g) in methylene chloride (70 mL, −30° C.) was added a solution of N-benzyloxycarbonyl-α-phosphonoglycine trimethyl ester (3.63 g) in methylene chloride (15 mL). The resulting solution was stirred 5 min and treated with the 2-methoxy-pyrimidine-5-carbaldehyde (1.0 g) in methylene chloride (15 mL). After stirring for 1.5 h, the reaction was warmed to 0° C. and stirred 1 h. The reaction was quickly poured into a sep funnel containing ethyl acetate and water. Brine was added to aid in separation of the layers. The aqueous was extracted with ethyl acetate (3×) which were in turn washed with brine, dried over magnesium sulfate, and concentrated. The crude product was recrystallized from hot methanol to give 1.4 g of pure material. Mass spec.: 344.10 (MH)+.

Workup

  1. stirringAfter stirring for 1.5 h
  2. stirringstirred 1 h
  3. additionThe reaction was quickly poured into a sep funnel
  4. customto aid in separation of the layers
  5. extractionThe aqueous was extracted with ethyl acetate (3×) which
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was recrystallized from hot methanol

Sources & evidence

ORD record
ord-abab795ac8c649e68e8d28a488af0da0
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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