p-Toluenesulfonic acid monohydrate → HCID 53671780, compound

HRID 234232Notes

Reaction equation

HRID 234232 reaction equation
[CH3:1][Si:2]([CH3:60])([C:54]([CH3:59])([CH3:58])[CH:55]([CH3:57])[CH3:56])[O:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[O:28])[CH2:14][CH2:13][C@H:12]([CH2:29][O:30]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:11][O:10][C:9](=[O:50])[C:8]=2[C:7]([CH3:51])=[C:6]([O:52][CH3:53])[CH:5]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:60][Si:2]([CH3:1])([C:54]([CH3:58])([CH3:59])[CH:55]([CH3:56])[CH3:57])[O:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[O:28])[CH2:14][CH2:13][C@H:12]([CH2:29][OH:30])[CH2:11][O:10][C:9](=[O:50])[C:8]=2[C:7]([CH3:51])=[C:6]([O:52][CH3:53])[CH:5]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 52937529HCID 52937529, compound

Product 1

HCID 53671780HCID 53671780, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4R,9R)-16-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-9-trityloxymethyl-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-6,12-dione was treated with 4-toluenesulfonic acid monohydrate in methanol at 20° C. for 30 min to yield (4R,9R)-16-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-9-hydroxymethyl-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin6,12-dione as a white foam.

Sources & evidence

ORD record
ord-eed48bf3ece94fdda05fb3c46b9588d5
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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