(2S)-2-[(4-fluorophenoxy)methyl]oxirane → 1'-[(2S)-3-(4-fluorophenoxy)-2-hydroxypropyl]-9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665416Notes

Reaction equation

HRID 1665416 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.[F:28][C:29]1[CH:39]=[CH:38][C:32]([O:33][CH2:34][C@@H:35]2[CH2:37][O:36]2)=[CH:31][CH:30]=1>>[F:28][C:29]1[CH:39]=[CH:38][C:32]([O:33][CH2:34][C@@H:35]([OH:36])[CH2:37][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:31][CH:30]=1

Participants

3

Reactant 2

HCID 6932898(2S)-2-[(4-fluorophenoxy)methyl]oxiraneHCID 582447679-Phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576618931'-[(2S)-3-(4-fluorophenoxy)-2-hydroxypropyl]-9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 225 was synthesized using 9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, (2S)-2-[(4-fluorophenoxy)methyl]oxirane and conditions outlined in procedure Z. M.p.=173-175° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.01 (d, J=1.2 Hz, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.87 (dd, J=1.6, 7.6 Hz, 1H), 7.76 (d, J=7.6 Hz, 2H), 7.57 (dd, J=7.6, 7.6 Hz, 2H), 7.52-7.47 (m, 1H), 7.10 (dd, J=8.8, 8.8 Hz, 2H), 6.94 (dd, J=4.4, 8.8 Hz, 2H), 4.88 (d, J=4.8 Hz, 1H), 3.97-3.95 (m, 2H), 3.87-3.82 (m, 1H), 3.11 (s, 2H), 2.87-2.78 (m, 2H), 2.54-2.39 (m, 4H), 2.03 (d, J=14.4 Hz, 2H), 1.87-1.81 (m, 2H); LCMS: 546 [M+H].

Sources & evidence

ORD record
ord-0b80eeb8439a423097eba1fa1c468f75
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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