Methanol → HCID 23078198, compound

HRID 2356231Notes

Reaction equation

HRID 2356231 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 198 (2.38 g) was dissolved in benzene (20 mL). To this solution, triethylamine (0.711 mL) and DPPA (1.10 mL) were added. The mixture was then stirred for 10 min at room temperature and for a further 1 hour and 30 min while being refluxed. Subsequently, methanol (3.76 mL) was added over 30 min and the mixture was stirred overnight. 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 dried over anhydrous magnesium sulfate. The dried organic phase was concentrated and the resulting residue was purified-on a silica gel chromatography (hexane:ethyl acetate=20:1 to 10:1) to give the desired product as a yellow oil (2.04 g).

Workup

  1. temperaturewhile being refluxed
  2. stirringthe mixture was stirred overnight
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationThe dried organic phase was concentrated

Sources & evidence

ORD record
ord-9fcb079270c04cfaa2e52d9ea0ce3439
Source dataset
uspto-grants-2010_07
Patent number
US07759326B2

Reaction notes

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