oxirane, 2-methyl-2-phenyl- → HCID 57662058, compound

HRID 1665374Notes

Reaction equation

HRID 1665374 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]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)[CH2:3][CH2:2]1.[CH3:22][C:23]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:25][O:24]1>>[OH:24][C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:25])[CH2:22][N:1]1[CH2:2][CH2:3][C:4]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)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 16398oxirane, 2-methyl-2-phenyl-HCID 57661820Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 57662058HCID 57662058, compound

Procedure

Compound 177 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, 2-methyl-2-phenyloxirane and conditions outlined in general procedure X. M.p.=117° C. (dec); 400 MHz 1H NMR (DMSO-d6) δ: 7.88 (d, J=8 Hz, 1H), 7.77 (d, J=4 Hz, 2H), 7.56 (d, J=4 Hz, 1H), 7.49 (d, J=7.2 Hz, 2H), 7.30 (t, J=7.2 Hz, 2H), 7.19 (t, J=7.2 Hz, 1H), 4.84 (bs, 1H), 3.05 (s, 2H), 2.72-2.34 (m, 2H), 1.96-1.83 (m, 4H), 1.80-1.57 (m, 4H), 1.47 (s, 3H). LCMS: 436 [M+H].

Sources & evidence

ORD record
ord-e56d1fa1408b42c0a2647b3c9d5c8775
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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