Triphenylphosphine → HCID 85323773, compound

HRID 1379668Notes

Reaction equation

HRID 1379668 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:50])[N:24]([CH:25]([CH2:42][CH2:43]O)[C:26]([NH:28][CH:29]([CH2:34][CH2:35][CH2:36][CH:37]([O:40][CH3:41])[O:38][CH3:39])[C:30]([O:32][CH3:33])=[O:31])=[O:27])[C:23](=[O:45])[C:22]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:21]12.[C:51]([OH:54])(=[S:53])[CH3:52]>O1CCCC1>[C:23]1(=[O:45])[N:24]([CH:25]([CH2:42][CH2:43][S:53][C:51](=[O:54])[CH3:52])[C:26]([NH:28][CH:29]([CH2:34][CH2:35][CH2:36][CH:37]([O:38][CH3:39])[O:40][CH3:41])[C:30]([O:32][CH3:33])=[O:31])=[O:27])[C:20](=[O:50])[C:21]2=[CH:49][CH:48]=[CH:47][CH:46]=[C:22]12

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 131720213HCID 131720213, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 85323773HCID 85323773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A cold (0° C.) solution of triphenylphosphine (1.143 g., 4.36 mmol.) in tetrahydrofuran (20 ml.) was treated with diisopropyl azidodicarboxylate (860 μl., 883 mg., 4.37 mmol.). Within 5 minutes a white slurry developed. After 30 minutes, a solution of [S-(R*,R*)-2-[(2-phthalimido-4-hydroxy-1-oxobutyl]-amino]-6,6-dimethoxyhexanoic acid, methyl ester [prepared as described in Example 1(f), 928 mg., 2.19 mmol.] in tetrahydrofuran (8 ml.) was added followed by neat thioacetic acid (312 μl., 332 mg., 4.36 mmol.). The mixture was stirred at 0° C. for 1.25 hours, then partitioned between 50% saturated sodium bicarbonate and ethyl acetate. The ethyl acetate extract was washed with brine, dried (sodium sulfate), filtered and stripped. The residue was redissolved in ethyl acetate and treated with a small amount of hexane to precipitate triphenylphosphine oxide. The mixture was filtered and the filtrate was flash chromatographed (Merck silica gel, 65:35-ethyl acetate:hexanes) to give 894 mg. of the title product as a colorless oil. TLC (75:25-ethyl acetate:hexanes) Rf =0.43.

Workup

  1. waitAfter 30 minutes
  2. custompartitioned between 50% saturated sodium bicarbonate and ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. dissolutionThe residue was redissolved in ethyl acetate
  8. additiontreated with a small amount of hexane
  9. customto precipitate triphenylphosphine oxide
  10. filtrationThe mixture was filtered
  11. customchromatographed (Merck silica gel, 65:35-ethyl acetate:hexanes)
  12. customto give 894 mg

Sources & evidence

ORD record
ord-3ad5e3ec98394909a4faa86bf6b87529
Source dataset
uspto-grants-1997_09
Patent number
US05672599

Reaction notes

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