2-Benzyloxirane, (R)- → 9-chloro-1'-[(2R)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665389Notes

Reaction equation

HRID 1665389 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]2[C:5]([C:6](=[O:22])[C:7](=[O:21])[C:8]3[S:18][CH2:17][C:11]4([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]4)[O:10][C:9]=32)=[CH:4][CH:3]=1.[CH2:23]([C@@H:30]1[CH2:32][O:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Cl:1][C:2]1[CH:20]=[C:19]2[C:5]([C:6](=[O:22])[C:7](=[O:21])[C:8]3[S:18][CH2:17][C:11]4([CH2:16][CH2:15][N:14]([CH2:32][C@H:30]([OH:31])[CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:13][CH2:12]4)[O:10][C:9]=32)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 110189162-Benzyloxirane, (R)-HCID 576620609-Chlorospiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576619479-chloro-1'-[(2R)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 194 was synthesized using 9-chlorospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, (2R)-2-benzyloxirane and conditions outlined in procedure Y. M.p.=92-93° C., 400 MHz 1H NMR (CDCl3) δ: 8.00-7.97 (d, J=8.21 Hz, 1H), 7.668-7.663 (d, J=1.95 Hz, 1H), 7.46-7.43 (dd, J=1.95, 8.21 Hz, 1H), 7.33-7.23 (m, 5H), 4.09-3.94 (m, 1H), 3.33 (br s, 1H), 2.88-2.82 (m, 4H), 2.75-2.70 (m, 3H), 2.52-2.41 (m, 3H), 2.14-2.11 (d, J=12.9 Hz, 2H), 1.94-1.80 (m, 2H); LCMS: 470 [M+H].

Sources & evidence

ORD record
ord-2299e4f4fa894c46b9405aefd7689baf
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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