Triphenylphosphine → HCID 86661405, compound

HRID 1908960Notes

Reaction equation

HRID 1908960 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39]([NH:41][C@H:42]([CH2:51]O)[CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35].S([O-])([O-])(=O)=O.[Mg+2]>O.C(OCC)(=O)C.O1CCCC1>[C:47]([O:46][C:44](=[O:45])[CH2:43][CH:42]1[CH2:51][N@@:41]1[C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:40])([CH3:48])([CH3:49])[CH3:50]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5363146Diisopropyl azodicarboxylateHCID 11616071tert-Butyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate

Product 1

HCID 86661405HCID 86661405, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2.90 g of triphenylphosphine and 15 mL of tetrahydrofuran were added to 100 mL flask and the resulting reaction solution was cooled to 0° C. 2.17 mL of diisopropylazodicarboxylate was dropped while the reaction solution was stirred. After 30 minutes, 10 mL of tetrahydrofuran solution with 1.52 g of (S)-t-butyl 3-(t-butoxycarbonylamino)-4-hydroxybutanoate was dropped and stirred for 16 hours while the reaction temperature was naturally increased to room temperature. After completing the reaction, 40 mL of ethyl acetate and 40 mL of water were added to the reaction solution and then stirred for 10 minutes. An organic layer was isolated, dehydrated with magnesium sulfate, and then concentrated under reduced pressure. A concentrated residue was isolated with column chromatography (n-hexane:ethyl acetate=15:1) and then concentrated under reduced pressure to obtain 1.04 g of a title compound.

Workup

  1. customthe resulting reaction solution
  2. stirringstirred for 16 hours while the reaction temperature
  3. temperaturewas naturally increased to room temperature
  4. additionwere added to the reaction solution
  5. stirringstirred for 10 minutes
  6. customAn organic layer was isolated
  7. concentrationconcentrated under reduced pressure
  8. customA concentrated residue was isolated with column chromatography (n-hexane:ethyl acetate=15:1)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c67559a558e540b7b72ed3374ccc11f6
Source dataset
uspto-grants-2013_12
Patent number
US08598347B2

Reaction notes

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