Dichloromethane → HCID 53769332, compound

HRID 376172Notes

Reaction equation

HRID 376172 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][CH2:13][CH3:14])=[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]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 76113BromotrimethylsilaneHCID 54076213HCID 54076213, compound

Product 1

HCID 53769332HCID 53769332, 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 ethyl 2(R)-amino-6-hydroxy-4-phosphonomethyl-hex-3-enoate. 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-de08c005849f461d9422d2d3c8223a95
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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