Benzyl Alcohol → HCID 53993169, compound

HRID 376176Notes

Reaction equation

HRID 376176 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]([CH2:23][P:24]([O:30]C(C)C)([O:26]C(C)C)=[O:25])=[CH:8][CH:9]([NH:20]C=O)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=[O:3])[CH3:2].C[Si](C)(C)Br.C(O)C1C=CC=CC=1>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][C:7]([CH2:23][P:24]([OH:26])([OH:30])=[O:25])=[CH:8][CH:9]([NH2:20])[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 76113BromotrimethylsilaneHCID 53780404HCID 53780404, compound

Product 1

HCID 53993169HCID 53993169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.75 g (3.6 mmol) of benzyl 6-acetoxy-2-formylamino-4-diisopropylphosphonomethyl-hex-3-enoate are dissolved in 15 ml of CH2Cl2. Then 1.88 ml (14.5 mmol) of trimethylbromosilane are added to this solution at room temperature. The reaction mixture is allowed to stand for 24 hours at room temperature. After addition of 15 ml of benzyl alcohol the reaction mixture is allowed to stand for 48 hours at room temperature and then concentrated by evaporation at 70° C. under a high vacuum. The residue is dissolved in 15 ml of ethanol and then a mixture of 15 ml of propylene oxide and 15 ml of ethanol is added dropwise to this solution. The suspension so obtained is stirred for 30 minutes in an ice bath and then filtered with suction. The crystals so obtained are recrystallised hot from ethanol/water and dried, giving white crystals of benzyl 6-acetoxy-2-amino-4-phosphonomethyl-hex-3-enoate. Melting point: 204°-205° C. (decomp.).

Workup

  1. waitto stand for 48 hours at room temperature
  2. concentrationconcentrated by evaporation at 70° C. under a high vacuum
  3. dissolutionThe residue is dissolved in 15 ml of ethanol
  4. additiona mixture of 15 ml of propylene oxide and 15 ml of ethanol
  5. additionis added dropwise to this solution
  6. customThe suspension so obtained
  7. filtrationfiltered with suction
  8. customThe crystals so obtained
  9. customare recrystallised hot from ethanol/water
  10. customdried

Sources & evidence

ORD record
ord-91f149d603304d3a9c613dc718918739
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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