Methanol → HCID 58022626, compound

HRID 445435Notes

Reaction equation

HRID 445435 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][C:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:26])C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:49][O-:50].[Na+].[Cl-].[NH4+:53].[CH3:54][OH:55]>C1C=CC=CC=1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][C:22]([NH:53][C:49]([O:55][CH3:54])=[O:50])([CH3:26])[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

8

Reactant 5

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 199401P,P-Diphenylphosphinic azideHCID 10942334Sodium MethoxideHCID 58022567HCID 58022567, compound

Product 1

HCID 58022626HCID 58022626, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the compound of Example 39 (15.8 g) in benzene (166 mL) was added diphenylphosphoryl azide (7.86 mL) and triethylamine (6.01 mL), and the resultant solution was heated to reflux for 1.5 hours. The temperature of the reaction solution was returned to room temperature, and methanol (20 mL) was added dropwise over 20 minutes. The resultant solution was heated to reflux for 30 minutes, and then further sodium methoxide (3.58 g) was added. The resultant solution was heated to reflux for 1.5 hours. To the reaction solution was added saturated aqueous ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the target product (15.6 g) as a colorless oil.

Workup

  1. temperatureto reflux for 1.5 hours
  2. customwas returned to room temperature
  3. temperatureto reflux for 30 minutes
  4. temperatureto reflux for 1.5 hours
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine in that order
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customthe resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ba05a2c5d142463f8a4839039a279922
Source dataset
uspto-grants-2013_07
Patent number
US08476305B2

Reaction notes

Loading…