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

HRID 1665407Notes

Reaction equation

HRID 1665407 reaction equation
[N: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)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]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[CH2:18][CH2:17][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]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:25]=5)[CH2:21][CH2:20]2)=[CH:34][CH:33]=1)([CH3:29])([CH3:30])[CH3:31]

Participants

3

Reactant 2

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-HCID 576619349-Morpholin-4-ylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576618251'-[(2S)-3-(4-tert-butylphenoxy)-2-hydroxypropyl]-9-morpholin-4-ylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 214 was synthesized using 9-morpholin-4-ylspiro[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.=107-109° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.74 (d, J=8.0 Hz, 1H), 7.25 (d, J=8.8 Hz, 2H), 7.18 (brs, 1H), 7.0 (d, J=8.8 Hz, 1H), 6.83 (d, J=8.4 Hz, 2H), 4.85 (brs, 1H), 3.91 (m, 2H), 3.82 (m, 1H), 3.74 (m, 4H), 3.43 (m, 4H), 3.05 (s, 2H), 2.76 (m, 2H), 2.43 (m, 4H), 1.97 (m, 2H), 1.78 (m, 2H), 1.22 (s, 9H); LCMS: 593 [M+H].

Sources & evidence

ORD record
ord-563d6bc2e0114d4ca7ac31697bd51b13
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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