4-tert-Butylphenyl glycidyl ether, (+)- → 1'-[(2S)-3-(4-tert-butylphenoxy)-2-hydroxypropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,3'-piperidine]-5,6-dione

HRID 1665392Notes

Reaction equation

HRID 1665392 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.[C:22]([C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C@@H:32]2[CH2:34][O:33]2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C@@H:32]([OH:33])[CH2:34][N:1]2[CH2:6][CH2:5][CH2:4][C:3]3([O:11][C:10]4[C:12]5[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=4[S:8][CH2:7]3)=[CH:16][CH:15]=[CH:14][CH:13]=5)[CH2:2]2)=[CH:28][CH:27]=1)([CH3:23])([CH3:24])[CH3:25]

Participants

3

Reactant 2

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-HCID 57662025Spiro[naphtho[1,2-b][1,4]oxathiine-2,3'-piperidine]-5,6-dione

Product 1

HCID 576619911'-[(2S)-3-(4-tert-butylphenoxy)-2-hydroxypropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,3'-piperidine]-5,6-dione

Procedure

Compound 197 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,3′-piperidine]-5,6-dione, (2S)-2-[(4-tert-butylphenoxy)methyl]oxirane and conditions outlined in procedure Y. M.p.=90-92° C., 400 MHz 1H NMR (CDCl3) δ: 8.04-8.02 (d, J=7.43 Hz, 1H), 7.75-7.73 (d, J=7.82 Hz, 1H), 7.63-7.58 (m, 1H), 7.48-7.44 (m, 1H), 7.31-7.21 (m, 2H), 6.83-6.80 (m, 1H), 4.13-4.07 (m, 1H), 3.15-2.96 (m, 3H), 2.82 (s, 1H), 2.65-2.50 (m, 5H), 2.04-1.73 (m, 4H), 1.29 (s, 9H); LCMS: 508 [M+H].

Sources & evidence

ORD record
ord-b930f5250708480aaa98012896b1a06e
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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