Potassium tert-butoxide → [3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenoxy]-acetic Acid
Reaction equation
[NH2:1][S:2]([N:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18](=[O:26])[O:19]CC[Si](C)(C)C)=[CH:12][C:11]=1[O:27]CC1C=CC=CC=1)[CH2:6][C:7](O)=[O:8])(=[O:4])=[O:3].CC(C)([O-])C.[K+]>>[OH:27][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][C:10]=1[N:5]1[CH2:6][C:7](=[O:8])[NH:1][S:2]1(=[O:4])=[O:3])[O:16][CH2:17][C:18]([OH:19])=[O:26]Participants
3
Procedure
The title compound is prepared from N-(aminosulfonyl)-N-(2-(benzyloxy)-4-{2-oxo-2-[2-(trimethylsilyl)ethoxy]ethoxy}phenyl)glycine analogous to Example 295, steps F and G with the modification of using two equivalents of potassium t-butoxide in step F: mp=185-188° C.; 1H NMR (DMSO-d6)δ 9.87 (br s, 1H), 7.22 (d, J=8.6 Hz, 1H), 6.43 (d, J=2.8 Hz, 1H), 6.38 (dd, J=8.8, 2.8 Hz, 1H), 4.62 (s, 2H), 4.32 (s, 2H); (M−1)−=301.
Sources & evidence
- ORD record
- ord-1fafdce77a59457eb1fac39d13d67451
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084448B2
Reaction notes
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