Benzenesulfonothioic acid, S-methyl ester → HCID 57324739, compound

HRID 2210713Notes

Reaction equation

HRID 2210713 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][O:4][C@@H:3]1[C@H:8]1[N:11]([Si](C)(C)C)[C:10](=[O:16])[C@@H:9]1[C@H:17]([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH3:18].[CH2:24]([O:27][C:28]([N:30]1[CH2:34][CH:33]([S:35]S(C2C=CC=CC=2)(=O)=O)[CH2:32][N:31]1[C:45]([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])=[O:29])[CH:25]=[CH2:26].C1(S(=O)(SC)=O)C=CC=CC=1>>[CH2:24]([O:27][C:28]([N:30]1[CH2:34][CH:33]([S:35][CH:7]2[CH2:6][CH2:5][O:4][C@H:3]([C@H:8]3[NH:11][C:10](=[O:16])[C@@H:9]3[C@H:17]([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH3:18])[C:2]2=[O:1])[CH2:32][N:31]1[C:45]([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])=[O:29])[CH:25]=[CH2:26]

Participants

4

Reactant 3

HCID 10899407Benzenesulfonothioic acid, S-methyl esterHCID 19379288HCID 19379288, compoundHCID 57115784HCID 57115784, compound

Product 1

HCID 57324739HCID 57324739, compound

Procedure

(3S,4S)-4-[(2R)-3-Oxotetrahydropyran-2-yl]-1-(trimethylsilyl) -3-[(R)-1-(trimethylsilyloxy)ethyl]azetidin-2-one was reacted as in Reference Example 38 except that 1,2-bis(allyloxycarbonyl)-4-phenylsulfonylthiopyrazolidine was used in lieu of S-methyl benzenethiosulfonate to give (3S,4S)-4-[(2R)-4-[[1,2-bis(allyloxycarbonyl)pyrazolidin-4-yl]thio]-3-oxotetrahydropyran-2-yl]-3-[(R)-1-(trimethylsilyloxy)ethyl]azetidin-2-one.

Sources & evidence

ORD record
ord-fe050bb283904d4fadcf0792ce0ee365
Source dataset
uspto-grants-1995_10
Patent number
US05459260

Reaction notes

Loading…