Triphenylphosphine → HCID 71682764, compound
Reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:20][CH2:21][O:22]C(/N=N/C(OCC)=O)=O.[C:32]([N:39]1[CH2:43][C@@H:42](O)[C@@H:41]([NH:45][S:46]([C:49]2[CH:54]=[CH:53][C:52]([O:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:51][CH:50]=2)(=[O:48])=[O:47])[CH2:40]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[S:62]1C=CC=C1CC(O)=O>C1COCC1>[C:32]([N:39]1[CH2:43][C@H:42]([S:62][C:21](=[O:22])[CH3:20])[C@@H:41]([NH:45][S:46]([C:49]2[CH:54]=[CH:53][C:52]([O:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[CH:51][CH:50]=2)(=[O:47])=[O:48])[CH2:40]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]Participants
Procedure
To a stirred solution of PPh3 (525 mg, 2.0 mmol) in THF (3 mL) at 0° C. was added DEAD (315 μL, 2.0 mmol) dropwise. After 10 min, a solution of (3S,4R)—N-Boc-3-(4-phenoxybenzenesulfonamido)-4-hydroxypyrrolidine (435 mg, 1.0 mmol) and thiolacetic acid (228 μL, 2.29 mmol) in THF (3 mL) was added. The resulting reaction mixture was stirred at room temperature for 6 hr, then it was concentrated under reduced pressure. The residue was purified be flash chromatography (15% ethyl acetate in hexane) to give (3S,4S)—N-Boc-3-(4-phenoxybenzenesulfonamido)-4-acetylthiopyrrolidine (400 mg, 81%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=9, 2H), 7.42 (m, 2H), 7.23 (t, J=8, 1H), 7.06 (m, 4H), 5.21 & 5.00 (br s, 1H, NH), 3.75 (m, 4H), 3.16 (m, 2H), 2.31 & 2.25 (br s, 3H), 1.44 (s, 9H); [α]20D=+22.8° (c=0.62, CHCl3).
Workup
- customThe resulting reaction mixture
- concentrationit was concentrated under reduced pressure
- customThe residue was purified
Sources & evidence
- ORD record
- ord-a423e53cd7544064bc0ebd78769a1dcb
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404866B2
Reaction notes
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