HCID 59849018, compound → HCID 86613530, compound

HRID 2237731Notes

Reaction equation

HRID 2237731 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][C@H:8]([CH:22]([CH3:24])[CH3:23])[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@@H:11]2[CH2:13][O:12]2)=[CH:5][C:4]=1[O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32]>C(O)(C)C.CN>[C:11]([CH2:10][NH:14][CH2:13][C@@H:11]([C@@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH2:9][C@H:8]([CH2:7][C:6]1[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[C:4]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:5]=1)[CH:22]([CH3:23])[CH3:24])[OH:12])(=[O:12])[CH3:13]

Participants

4

Reactant 1

HCID 59849018HCID 59849018, compound

Product 1

HCID 86613530HCID 86613530, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6329MethylamineSolvent

Procedure

A solution of 0.050 g of tert-butyl {3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methyl-1(S)-(R)-oxiranylpentyl}carbamate (Example 1b) in 1.0 ml of isopropanol and 0.10 ml of methylamine is stirred at 60° C. over 2 hours. The reaction mixture is concentrated by evaporation to dryness. The residue is dissolved in 2 ml of dichloromethane, admixed successively with 0.017 ml of pyridine and 0.026 ml of acetic anhydride and stirred at room temperature over 1 hour. The reaction solution is admixed with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with 1M HCl, water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.13 (95:5 dichloromethane-methanol); Rt=4.47 (gradient I).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation to dryness
  2. dissolutionThe residue is dissolved in 2 ml of dichloromethane
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. washThe combined organic phases are washed successively with 1M HCl, water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c6bcffeee5b842d3877d6288cfb76264
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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