Pyridine → HCID 86754760, compound

HRID 1602048Notes

Reaction equation

HRID 1602048 reaction equation
C(O[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][NH:7][C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])(=O)C.[CH2:20]([O:23]C(NCC(C1C=CC=CC=1)O)=O)C=C.[C:36]([O:39][C:40](=[O:42])[CH3:41])(=O)C.N1C=CC=C[CH:44]=1>>[CH3:36][O:39][C:40]([C:41]1[CH2:44][C:15]2[C:14]([CH2:5][C:6]=1[NH:7][C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:20])=[O:42]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 15246527HCID 15246527, compound2×HCID 15247504HCID 15247504, compound

Product 1

HCID 86754760HCID 86754760, compoundYield 83%

Procedure

Synthesis of N-Allyloxycarbonyl-2-amino-1-phenylethanol acetate (26) as illustrated in FIG. 5. reaction 5: ##STR14## Compound 26: Chemical method: Racemic N-allyloxycarbonyl-2-amino-1-phenylethanol 25 (51 mg, 0.23 mmol; see chemical synthesis for 23) was dissolved in dry pyridine (0.5 mL) and treated with acetic anhydride (0.33 mL, mmol). After stirring for 4 hours. at rt, the mixture was concentrated to a small volume in vacuo, dissolved in EtOAc, washed with 1N KHSO4 and brine, dried (MgSO4), filtered and concentrated in vacuo. Silica gel column chromatography (eluent: hexanes/EtOAc, 4/1, with gradient to 3/1, v/v) gave the desired product (50 mg) as an oil in 83% yield.

Workup

  1. concentrationat rt, the mixture was concentrated to a small volume in vacuo
  2. dissolutiondissolved in EtOAc
  3. washwashed with 1N KHSO4 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98105240da0c4154b7b11948639b4c2b
Source dataset
uspto-grants-1999_11
Patent number
US05981267

Reaction notes

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