4-tert-Butylphenyl glycidyl ether, (+)- → 1'-[(2S)-3-(4-tert-butylphenoxy)-2-hydroxypropyl]-9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665405Notes

Reaction equation

HRID 1665405 reaction equation
[C:1]1([C:7]2[CH:25]=[C:24]3[C:10]([C:11](=[O:27])[C:12](=[O:26])[C:13]4[S:23][CH2:22][C:16]5([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]5)[O:15][C:14]=43)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28]([C:32]1[CH:42]=[CH:41][C:35]([O:36][CH2:37][C@@H:38]2[CH2:40][O:39]2)=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29]>>[C:28]([C:32]1[CH:42]=[CH:41][C:35]([O:36][CH2:37][C@@H:38]([OH:39])[CH2:40][N:19]2[CH2:20][CH2:21][C:16]3([O:15][C:14]4[C:24]5[C:10]([C:11](=[O:27])[C:12](=[O:26])[C:13]=4[S:23][CH2:22]3)=[CH:9][CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:25]=5)[CH2:17][CH2:18]2)=[CH:34][CH:33]=1)([CH3:29])([CH3:30])[CH3:31]

Participants

3

Reactant 2

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-HCID 582447679-Phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576620481'-[(2S)-3-(4-tert-butylphenoxy)-2-hydroxypropyl]-9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 212 was synthesized using 9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, (2S)-2-[(4-tert-butylphenoxy)methyl]oxirane and conditions outlined in procedure Y. M.p.=151-152° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.98 (m, 2H), 7.86 (d, J=7.6 Hz, 1H), 7.76 (d, J=8.0 Hz, 2H), 7.53 (m, 3H), 7.28 (m, 2H), 6.85 (m, 2H), 4.85 (brs, 1H), 3.98 (brm, 3H), 3.10 (s, 2H), 2.82 (m, 2H), 2.44 (m, 4H), 2.0 (m, 2H), 1.80 (m, 2H), 1.20 (s, 9H); LCMS: 584 [M+H].

Sources & evidence

ORD record
ord-265e1eedeb22446a90244c706d913e49
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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