Triphenylphosphine → Benzyl 3-acetylsulfanylazetidine-1-carboxylate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][CH2:21][O:22]C(/N=N/C(OCC)=O)=O.[S:32]1C=CC=C1CC(O)=O.[CH2:41]([O:48][C:49]([N:51]1[CH2:54][CH:53](O)[CH2:52]1)=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1>[C:21]([S:32][CH:53]1[CH2:54][N:51]([C:49]([O:48][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:50])[CH2:52]1)(=[O:22])[CH3:20]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To triphenylphosphine (4.40 g, 16.8 mmol) in tetrahydrofuran (25 mL, THF) at -78 ° C. was added diethylazodicarboxylate (2.60 mL, 16.5 mmol) in THF (15 mL). After 7 min thiolacetic acid (1.25 mL, 17.5 mmol) in THF (15 mL) was added followed by, after 7 min, the resultant compound from Example 112 (2.789 g, 13.46 mmol). The mixture was stirred at -78 ° C. for 1 h and at room temperature for 20 h, and was then evaporated and chromatographed on silica gel with 20% ethyl acetate in hexane affording 3.250 g (91%) of a white solid, m.p. 94.5°-95.5 ° C. TLC (20% ethyl acetate/80% hexane) Rf =0.17; 1H NMR (CDCl3) 7.28-7.41 (m, 5H), 5.09 (s, 2H), 4.48 (d, 1H), 4.44 (d, 1H), 4.15-4.26 (m, 1H), 3.92 (d, 1H), 3.89 (d, 1H) 2.34 (s, 3H).
Workup
- customafter 7 min
- customwas then evaporated
- customchromatographed on silica gel with 20% ethyl acetate in hexane affording 3.250 g (91%) of a white solid, m.p. 94.5°-95.5 ° C
Sources & evidence
- ORD record
- ord-4230ee81c9bf4893a43dfa37d6141db2
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05258362
Reaction notes
Loading…