Dichloromethane → HCID 53739954, compound

HRID 487506Notes

Reaction equation

HRID 487506 reaction equation
C([O:4][CH2:5][CH2:6][C:7]([CH2:18][P:19]([O:25]C(C)C)([O:21]C(C)C)=[O:20])=[CH:8][C@@H:9]([NH:15]C=O)[C:10]([O:12]CC)=[O:11])(=O)C.C(Cl)Cl.C[Si](C)(C)Br>C(O)C>[NH2:15][C@H:9]([CH:8]=[C:7]([CH2:18][P:19]([OH:25])([OH:21])=[O:20])[CH2:6][CH2:5][OH:4])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 76113BromotrimethylsilaneHCID 54076213HCID 54076213, compound

Product 1

HCID 53739954HCID 53739954, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

12.7 g (30.2 mmol) of ethyl 6-acetoxy-2(R)-formylamino-4-diisopropylphosphonomethyl-hex-3-enoate are dissolved in 100 ml of abs. CH2Cl2 and 15.6 ml (120.8 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 100 ml of abs. ethanol the reaction mixture is again allowed to stand for 24 hours at room temperature and then concentrated by evaporation. The residue is dissolved in ethanol and then a mixture of 100 ml of propylene oxide and 100 ml of ethanol is added dropwise. The suspension so obtained is stirred for 1 hour at 0° C. and then filtered with suction. The filter product is stirred overnight in ether and again filtered with suction. The filter product is dried, giving white crystals of 2(R)-amino-6-hydroxy-4-phosphonomethyl-hex-3-enoic acid. Melting point: 170° C. (decomp.). ee=92%; αD =-45.6°± 1° (c=1.0 H2O).

Workup

  1. additionAfter addition of 100 ml of abs
  2. waitto stand for 24 hours at room temperature
  3. concentrationconcentrated by evaporation
  4. dissolutionThe residue is dissolved in ethanol
  5. additiona mixture of 100 ml of propylene oxide and 100 ml of ethanol
  6. additionis added dropwise
  7. customThe suspension so obtained
  8. filtrationfiltered with suction
  9. stirringThe filter product is stirred overnight in ether
  10. filtrationagain filtered with suction
  11. customThe filter product is dried

Sources & evidence

ORD record
ord-124ac145eda440a1b821bb2efd2e11bf
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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