Triphenylphosphine → HCID 131720214, compound

HRID 1379669Notes

Reaction equation

HRID 1379669 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC([O:24][CH:25]([CH3:27])C)=O.[C:34]1(=[O:63])[N:38]([CH:39]([CH2:55][CH2:56]O)[C:40]([NH:42][CH:43]([CH2:48][CH2:49][CH:50]([O:53][CH3:54])[O:51][CH3:52])[C:44]([O:46][CH3:47])=[O:45])=[O:41])[C:37](=[O:58])[C:36]2=[CH:59][CH:60]=[CH:61][CH:62]=[C:35]12.[S:64]1C=CC=C1CC(O)=O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[C:37]1(=[O:58])[N:38]([CH:39]([CH2:55][CH2:56][S:64][C:25](=[O:24])[CH3:27])[C:40]([NH:42][CH:43]([CH2:48][CH2:49][CH:50]([O:53][CH3:54])[O:51][CH3:52])[C:44]([O:46][CH3:47])=[O:45])=[O:41])[C:34](=[O:63])[C:35]2=[CH:62][CH:61]=[CH:60][CH:59]=[C:36]12

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 131720215HCID 131720215, compound

Product 1

HCID 131720214HCID 131720214, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of triphenylphosphine (1.26 g., 4.79 mmol., 1.5 eq.) in dry tetrahydrofuran (15 ml.) was treated with diisopropyl azodicarboxylate (943 μl., 4.79 mmol.). The resultant white slurry was stirred for 30 minutes and then treated with a solution of [S-(R*,R*)]-2-[(2-phthalimido-4-hydroxy-1-oxobutyl)amino]-5,5-dimethoxypentanoic acid, methyl ester [prepared as described in Example 4(i), 1,35 g., 3.20 mmol.]in dry tetrahydrofuran (15 ml.) followed by neat thiolacetic acid (343 μl., 4.79 mmol.). The mixture was stirred at 0° C. for 1.5 hours and then partitioned between ethyl acetate (150 ml.) and 50% sodium bicarbonate (100 ml.). The ethyl acetate layer was washed with brine, dried over magnesium sulfate, filtered, concentrated, adsorbed onto Celite® and dried in vacuo. The crude material was purified by chromatography on a 2.5×15 cm silica gel column eluting with 1:1 ethyl acetate:hexane (11.) and 6:4 ethyl acetate:hexane (11.). The desired fractions were combined, concentrated and dried in vacuo affording 1.35 g. of title produce as an oil. TLC (8:2, ethyl acetate:hexane) Rf =0.42.

Workup

  1. customprepared
  2. stirringThe mixture was stirred at 0° C. for 1.5 hours
  3. custompartitioned between ethyl acetate (150 ml.) and 50% sodium bicarbonate (100 ml.)
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo
  9. customThe crude material was purified by chromatography on a 2.5×15 cm silica gel column
  10. washeluting with 1:1 ethyl acetate
  11. concentrationconcentrated
  12. customdried in vacuo
  13. customaffording 1.35 g
  14. customof title produce as an oil

Sources & evidence

ORD record
ord-ba9c6f4fd93f4f02a103d3aa76d36fb2
Source dataset
uspto-grants-1997_09
Patent number
US05672599

Reaction notes

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