Tetrahydrofuran → HCID 74016630, compound

HRID 272286Notes

Reaction equation

HRID 272286 reaction equation
[CH2:1]([P:6](=[O:11])([O-:10])[O:7][CH2:8][CH3:9])P(=O)([O-])[O-].[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([S:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][CH:36]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH:37]=O)=[C:29]([Cl:47])[CH:28]=2)[CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+].[CH2:50]1COC[CH2:51]1>>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([S:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][CH:36]([NH:39][C:40]([O:42][C:43]([CH3:45])([CH3:46])[CH3:44])=[O:41])[CH:37]=[CH:1][P:6](=[O:11])([O:10][CH2:50][CH3:51])[O:7][CH2:8][CH3:9])=[C:29]([Cl:47])[CH:28]=2)[CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 59837306HCID 59837306, compoundHCID 131727193HCID 131727193, compound

Product 1

HCID 74016630HCID 74016630, compound

Procedure

Ethyl methylenebisphosphonate (940 mg) in THF (5 mL) was chilled to −78° C. under an argon gas atmosphere. To this solution, a 1.6 mol/L n-BuL-hexane solution (2 mL) was added dropwise and the mixture was stirred for 30 min, followed by dropwise addition of a THF solution (15 mL) of the compound of Example 193 (1.58 g). After 3 hours, a saturated ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous solution of sodium chloride and was dried over anhydrous sodium sulfate. The solvent was removed by distillation to give the desired product as a colorless oil (1.71 g).

Workup

  1. waitAfter 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and was dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-3cddc6cbe8ac4e2785d7039ee39e53b5
Source dataset
uspto-grants-2008_11
Patent number
US07456157B2

Reaction notes

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