Triphenylphosphine → HCID 67248558, compound

HRID 1027573Notes

Reaction equation

HRID 1027573 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[S:32]1[CH2:35][CH:34](O)[CH2:33]1.[C:37]([O:41][C:42](=[O:50])[NH:43][CH:44]1[CH2:48][O:47][NH:46][C:45]1=[O:49])([CH3:40])([CH3:39])[CH3:38]>C1COCC1>[C:37]([O:41][C:42](=[O:50])[NH:43][C@@H:44]1[CH2:48][O:47][N:46]([CH:34]2[CH2:35][S:32][CH2:33]2)[C:45]1=[O:49])([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 825323-Thietan-1-olHCID 5225473HCID 5225473, compoundHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 67248558HCID 67248558, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of triphenylphosphine (0.79 g) in THF (22 ml) was cooled under argon to −10° C. Diethylazodicarboxylate (DEAD, 1.57 g) was added dropwise then thietan-3-ol (0.4 g) and (3-oxo-isoxazolidin-4-yl)-carbamic acid tert-butyl ester (0.27 g, prepared from (D)-cycloserine as described in Chem. Pharm. Bull. 2002, 50(4) 554-557). The reaction mixture was stirred at room temperature for 24 hours then the solvent was removed in vacuo. The crude product was purified by column chromatography (eluent cyclohexane/ethyl acetate) to afford the title product as a white solid (51 mg). 1H-NMR (CDCl3, 400 MHz): 5.45 (q, 1H), 5.05 (m, 1H), 4.90 (m, 1H), 4.50 (t, 1H), 4.10 (dd, 1H), 3.55 (m, 2H), 3.40 (m, 2H), 1.50 (s, 9H).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude product was purified by column chromatography (eluent cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-ad2c8d0ca0a0433fb853142afab9d599
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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