Ethyl Acetate → HCID 178450815, compound

HRID 2169249Notes

Reaction equation

HRID 2169249 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[C:10]1([CH2:15][C:16]([NH2:18])=[NH:17])[CH2:14][CH2:13][CH2:12][CH2:11]1.[C:19]([O:23][C:24](=[O:39])/[C:25](/O)=[C:26](\[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)/[C:27](O)=[O:28])([CH3:22])([CH3:21])[CH3:20].C(OCC)(=O)C>CO.CCCCCC>[C:19]([O:23][C:24]([C:25]1[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:27]([OH:28])[N:18]=[C:16]([CH2:15][C:10]2([C:4]3[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:3]=3[Cl:2])[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:17]=1)=[O:39])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl esterHCID 867258982-[1-(2,5-Dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride

Product 1

HCID 178450815HCID 178450815, compoundYield 53.55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 2-[1-(2,5-dichlorophenyl)-cyclopentyl]-acetamidine hydrochloride (2=3) (2.0, 7.407 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester (4) (3.422 g, 11.111 mmol) in methanol (50 mL) NaOMe (25% in methanol; 4.8 mL) was added dropwise at 0° C. and stirred at room temperature for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.6). The reaction mixture was quenched with HCl (1N; 5 mL), methanol was removed, the product was diluted with water and the mixture was extracted with ethyl acetate. The combined organic part was dried, the product was concentrated and the crude product was purified using a normal silica gel column using a gradient eluent of 10 to 40% ethyl acetate in hexane to get pure 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (204) (2.1 g, 53.55%) as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with HCl (1N; 5 mL), methanol
  2. customwas removed
  3. additionthe product was diluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe combined organic part was dried
  6. concentrationthe product was concentrated
  7. customthe crude product was purified

Sources & evidence

ORD record
ord-9208057309df4b7ab9ce11dc4a8ac5a6
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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