Triphenylphosphine → HCID 53923612, compound

HRID 1107178Notes

Reaction equation

HRID 1107178 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH:34]([CH:38]([S:49]([C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=1)(=[O:51])=[O:50])[CH2:39][CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:35]([OH:37])=O>C1COCC1>[CH3:59][O:58][C:55]1[CH:54]=[CH:53][C:52]([S:49]([C@@H:38]([C@@H:34]2[CH2:35][O:37][C:33]2=[O:32])[CH2:39][CH2:40][CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)(=[O:50])=[O:51])=[CH:57][CH:56]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69906473HCID 69906473, compound

Product 1

HCID 53923612HCID 53923612, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

Diethyl azodicarboxylate (0.45 mL, 2.7 mmol) is added dropwise to a solution of triphenyl phosphine (0.71 g, 2.7 mmol) in THF (18 mL) at -78° C. After 15 minutes a solution of (±)-(2R*, 3R*)-2-Hydroxymethyl-3-(4-methoxybenzenesulfonyl)-7-phenylheptanoic acid (1 g, 2.5 mmol) in THF (8 mL) is added dropwise over 5 minutes. After 30 minutes the bath is removed and the reaction is allowed to warm to 23° C. and stir for 45 minutes. The reaction is concentrated in vacuo and the crude reaction mixture is purified by column chromatography (silica, CH2Cl2) to yield pure (±)-3-(R*)-[1-(R*)-(4-methoxybenzenesulfonyl)-5-phenypentyl]oxetan-2-one (0.63 g, 63%): 1H NMR (300 MHz, CDCl3) δ 7.75-7.70 (m, 2H), 7.28-7.23 (m, 2H), 7.19-7.14 (m, 1H), 7.12-7.09 (m, 2H), 7.03-6.95 (m, 2H), 4.41 (t, J=6.2 Hz, 1H), 4.31 (t, J=5.4 Hz, 1H), 4.03-3.95 (m, 1H), 3.87 (s, 3H), 3.44-3.37 (m, 1H), 2.53 (t, J=7.2 Hz, 2H), 1.89-1.81 (m, 2H), 1.58-1.38 (m, 4H); 13C NMR (75.5 MHz, CDCl3) δ 167.83, 164.25, 141.89, 130.91, 128.21, 128.17, 125.65, 114.65, 113.91, 65.04, 63.83, 55.68, 50.47, 35.16, 30.91, 27.04, 25.73; MS (FAB) m/e 389 (M+H)+.

Workup

  1. customAfter 30 minutes the bath is removed
  2. concentrationThe reaction is concentrated in vacuo
  3. customthe crude reaction mixture
  4. customis purified by column chromatography (silica, CH2Cl2)

Sources & evidence

ORD record
ord-12d7573bcd6949b6afb0c0a466be73cc
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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