Isopropanol → HCID 54565818, compound

HRID 1448425Notes

Reaction equation

HRID 1448425 reaction equation
[CH:1](O)([CH3:3])[CH3:2].C(N(CC)CC)C.[F:12][C:13]([F:32])([F:31])[C:14]([N:16]([CH2:24][P:25]([O:29]Cl)([O:27]Cl)=[O:26])[CH2:17][C:18]([O:20][CH2:21][CH2:22][Cl:23])=[O:19])=[O:15].[CH:33]([NH2:36])([CH3:35])[CH3:34]>O1CCCC1.CCOCC>[F:12][C:13]([F:32])([F:31])[C:14]([N:16]([CH:24]([CH:1]([CH3:3])[CH3:2])[P:25]([OH:29])([O:27][NH:36][CH:33]([CH3:35])[CH3:34])=[O:26])[CH2:17][C:18]([O:20][CH2:21][CH2:22][Cl:23])=[O:19])=[O:15]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 6363IsopropylamineHCID 8471TriethylamineHCID 54009859HCID 54009859, compound

Product 1

HCID 54565818HCID 54565818, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of isopropanol (1.0 ml, 0.025 mole) and triethylamine (3.5 ml, 0.025 mole) in 50 ml. of tetrahydrofuran was added to a solution of β-chloroethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (9.1 g, 0.025 mole) in 250 ml. of ether at 0° C. After three hours, the solution was filtered and the filtrate was added to a cooled (0° C.) solution of isopropylamine (4.2 ml, 0.05 mole) in 50 ml. of tetrahydrofuran. After stirring for 16 hours at 25° C., the reaction mixture was filtered and the filtrate was concentrated in vacuo. The residual oil was dissolved in methylene chloride and washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution. The solution was dried over sodium sulfate and concentrated in vacuo to yield a solid. Recrystallization from ethyl acetate-hexane (1:10) yielded β-chloroethyl N-trifluoroacetyl-N-(isopropyl(isopropylamino)phosphonomethyl)glycinate as a white solid, m.p. 87.5°-89° C.

Workup

  1. customat 0° C
  2. filtrationthe solution was filtered
  3. additionthe filtrate was added to
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe residual oil was dissolved in methylene chloride
  7. washwashed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution
  8. dry with materialThe solution was dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto yield a solid
  11. customRecrystallization from ethyl acetate-hexane (1:10)

Sources & evidence

ORD record
ord-468c8d0c1b254397820305cdc15f7d98
Source dataset
uspto-grants-1979_12
Patent number
US04180394

Reaction notes

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