p-Toluenesulfonic acid monohydrate → 1,3,4-Thiadiazole-2-ethanol, beta-amino-beta-methyl-5-[4-(octyloxy)-3-(trifluoromethyl)phenyl]-, (betaS)-

HRID 2357102Notes

Reaction equation

O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC1(C)[N:18](C(OC(C)(C)C)=O)[C@@:17]([CH3:50])([C:26]2[S:27][C:28]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[C:33]([C:46]([F:49])([F:48])[F:47])[CH:32]=3)=[N:29][N:30]=2)[CH2:16][O:15]1>CO>[NH2:18][C@@:17]([C:26]1[S:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[C:33]([C:46]([F:47])([F:49])[F:48])[CH:32]=2)=[N:29][N:30]=1)([CH3:50])[CH2:16][OH:15]

Participants

Conditions

Temperature: 20.5 °C

Procedure

A 5 L round bottom flask was inerted and charged with p-toluene sulfonic acid monohydrate (208 g, 1.09 mol, 5 equiv) and a solution of (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate (125 g, 0.22 mol) in methanol (2.5 L), and heated to reflux. After 1.5 h HPLC indicated reaction complete. The heat was turned off and the mixture was allowed to cool to room temperature (18 to 23° C.) and stirred for 12 hours. The mixture was concentrated under vacuum to a residue to provide the title product.

Workup

customA 5 L round bottom flask was inerted
customreaction complete
concentrationThe mixture was concentrated under vacuum to a residue

Sources & evidence

ORD record: ord-b7a492536991418d8390acc57769f61d
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759370B2

Reaction notes

Loading…