2-Benzyloxirane, (S)- → 1'-[(2S)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,3'-piperidine]-5,6-dione

HRID 1665391Notes

Reaction equation

HRID 1665391 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C:3]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:2]1.[CH2:22]([C@H:29]1[CH2:31][O:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[OH:30][C@@H:29]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:31][N:1]1[CH2:6][CH2:5][CH2:4][C:3]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:2]1

Participants

3

Reactant 2

HCID 110189152-Benzyloxirane, (S)-HCID 57662025Spiro[naphtho[1,2-b][1,4]oxathiine-2,3'-piperidine]-5,6-dione

Product 1

HCID 576618171'-[(2S)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,3'-piperidine]-5,6-dione

Procedure

Compound 196 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,3′-piperidine]-5,6-dione, (2S)-2-benzyloxirane and conditions outlined in procedure Y. M.p.=59-60° C., 400 MHz 1H NMR (CDCl3) δ: 8.05-8.03 (br d, J=7.43 Hz, 1H), 7.73-7.70 (m, 1H), 7.65-7.60 (m, 1H), 7.52-7.44 (m, 1H), 7.31-7.18 (m, 5H), 3.95-3.91 (m, 1H), 3.18-2.91 (m, 3H), 2.78-2.53 (m, 5H), 2.45-2.33 (m, 2H), 2.03-1.71 (m, 4H); LCMS: 436 [M+H].

Sources & evidence

ORD record
ord-034957e89b6e4ff6a369753faa333779
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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