Methanol → HCID 23078198, compound

HRID 1455788Notes

Reaction equation

HRID 1455788 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([C:30]([O:32][CH2:33][CH3:34])=[O:31])([CH3:29])C(O)=O)=[C:18]([Cl:35])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:38]([CH2:41]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[CH3:60][OH:61].[OH2:62]>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([NH:38][C:41]([O:61][CH3:60])=[O:62])([CH3:29])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:18]([Cl:35])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59837328HCID 59837328, compound

Product 1

HCID 23078198HCID 23078198, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The compound of Example 156 (2.38 g) was dissolved in benzene (20 mL). To this solution, triethylamine (0.711 mL) and DPPA (1.10 mL) were added and the mixture was stirred at room temperature for 10 min, was refluxed, and was further stirred for 1 hour and 30 min. Methanol (3.76 mL) was added over a 30 minute-time period and the mixture was stirred overnight. Subsequently, the reaction mixture was diluted with water and was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, and was then dried over anhydrous magnesium sulfate and was concentrated. The residue was purified on a silica gel column chromatography (hexane:ethyl acetate=20:1 shifted to 5:1) to give the desired product as a yellow oil (2.04 g).

Workup

  1. temperaturewas refluxed
  2. stirringwas further stirred for 1 hour and 30 min
  3. stirringthe mixture was stirred overnight
  4. extractionwas extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. concentrationwas concentrated
  8. customThe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=20:1 shifted to 5:1)

Sources & evidence

ORD record
ord-40d6d59668e245abbfd8c39a96313c53
Source dataset
uspto-grants-2009_01
Patent number
US07482491B2

Reaction notes

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