Acetonitrile--water (1/1) → (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(4-phenylbutoxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate

HRID 2357067Notes

Reaction equation

HRID 2357067 reaction equation
[CH3:1][C:2]1([CH3:39])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@:5]([CH3:38])([C:14]2[S:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[C:21]([C:34]([F:37])([F:36])[F:35])[CH:20]=3)=[N:17][N:18]=2)[CH2:4][O:3]1.[C:40](#N)[CH3:41].O>>[CH3:39][C:2]1([CH3:1])[N:6]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@@:5]([CH3:38])([C:14]2[S:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]4[CH:41]=[CH:40][CH:33]=[CH:32][CH:31]=4)=[C:21]([C:34]([F:37])([F:36])[F:35])[CH:20]=3)=[N:17][N:18]=2)[CH2:4][O:3]1

Participants

3

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 59384428(R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate

Product 1

HCID 59384351(R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(4-phenylbutoxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylateYield 75%

Procedure

The title compound was prepared analogously to (R)-tert-butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate (14a) in 75% yield. MS (ESI): 592.14 (MH+), HPLC retention time on a C8(2) column (30×3.00 mm, 3μ) is 3.55 min with gradient 50-98% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase

Sources & evidence

ORD record
ord-83748f49187641b4b906097e7093b5a4
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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