Triphenylphosphine → HCID 131722585, compound

HRID 1978817Notes

Reaction equation

HRID 1978817 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([NH:39][C@H:40]([C:45]([NH:47][C@H:48]([CH2:53]O)[CH2:49][CH:50]([CH3:52])[CH3:51])=[O:46])[C:41]([CH3:44])([CH3:43])[CH3:42])=[O:38])([CH3:35])([CH3:34])[CH3:33].[C:55]([OH:58])(=[S:57])[CH3:56]>C1COCC1>[C:32]([O:36][C:37]([NH:39][C@H:40]([C:45]([NH:47][C@H:48]([CH2:53][S:57][C:55](=[O:58])[CH3:56])[CH2:49][CH:50]([CH3:52])[CH3:51])=[O:46])[C:41]([CH3:42])([CH3:43])[CH3:44])=[O:38])([CH3:33])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86756857HCID 86756857, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 131722585HCID 131722585, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution triphenylphosphine (373 mg, 1.42 mmol) and diethyl azodicarboxylate (225 μL, 1.42 mmol) in THF (6 mL) at 0° was added a solution of N-tert-butyloxy carbonyl-L-tert-butylglycyl-L-leucinol 10 (313 mg, 0.950 mmol) and thioacetic acid (100 μL, 1.42 mmol) in THF (4 mL). The mixture was stirred at 0° for 2 h and the solvent was removed under vacuum. The residue was purified by flash chromatography (SiO2, 10-30% EtOAc-hexane) to give the corresponding title compound 11 in 63% yield (232 mg).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residue was purified by flash chromatography (SiO2, 10-30% EtOAc-hexane)

Sources & evidence

ORD record
ord-37fe2fcb504647399dbad18115b6cb1f
Source dataset
uspto-grants-2001_05
Patent number
US06239125B1

Reaction notes

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