Potassium → HCID 22811227, compound

HRID 1706187Notes

Reaction equation

HRID 1706187 reaction equation
[OH:1][C@H:2]([CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[K].[CH2:37]([O:39][C:40]([O:42][NH:43][C:44](=[O:48])[O:45][CH2:46][CH3:47])=[O:41])[CH3:38]>CN(C)C=O>[CH2:46]([O:45][C:44]([N:43]([CH2:12][C@@H:2]([OH:1])[CH2:3][P:4](=[O:11])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])[O:42][C:40]([O:39][CH2:37][CH3:38])=[O:41])=[O:48])[CH3:47]

Participants

6

Reactant 4

HCID 5462222Potassium2×HCID 11446651Ethyl Ethoxycarbonyloxycarbamate2×HCID 11708267BistrimethylsilylacetamidHCID 22811226HCID 22811226, compound

Product 1

HCID 22811227HCID 22811227, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Diethyl 2(R)-hydroxy-3-tosyloxypropylphosphonate (7.3 g) was dissolved in N,N-dimethylformamide (100 ml). To the solution was added bis(trimethylsilyl)acetamide (12.2 g) under ice-cooling. After the mixture was stirred for 30 minutes at the same temperature, potassium salt of ethyl N-ethoxycarbonyloxycarbamate (5.16 g) was added thereto. The reaction mixture was stirred for 10 hours at 70° C. To this reaction mixture was added potassium salt of ethyl N-ethoxycarbonyloxycarbamate (0.86 g) and then the reaction mixture was further stirred for 2 hours at 70° C. After the resultant mixture was concentrated under reduced pressure, to the oily residue was added a mixture of ethyl acetate (200 ml) and 2% hydrochloric acid (100 ml). The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and then concentrated under reduced pressure to give oily diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2(R)-hydroxypropylphosphonate (7.05 g).

Workup

  1. temperaturecooling
  2. additionwas added
  3. stirringthe reaction mixture was further stirred for 2 hours at 70° C
  4. concentrationAfter the resultant mixture was concentrated under reduced pressure, to the oily residue
  5. additionwas added
  6. additiona mixture of ethyl acetate (200 ml) and 2% hydrochloric acid (100 ml)
  7. customThe ethyl acetate layer was separated
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5bd39b557d24b4b8c65bb84829ad608
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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