Sodium Hydroxide → HCID 59226714, compound
Reaction equation
C([O:5][C:6](=[O:32])[CH2:7][CH2:8][N:9]([CH2:25][C:26]1[S:27][C:28]([CH3:31])=[CH:29][CH:30]=1)[C:10]1[S:11][CH:12]=[C:13]([CH:15]2[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]([CH3:24])([CH3:23])[CH2:16]2)[N:14]=1)(C)(C)C.[OH-].[Na+]>>[CH3:31][C:28]1[S:27][C:26]([CH2:25][N:9]([C:10]2[S:11][CH:12]=[C:13]([CH:15]3[CH2:16][C:17]([CH3:24])([CH3:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH2:20]3)[N:14]=2)[CH2:8][CH2:7][C:6]([OH:32])=[O:5])=[CH:30][CH:29]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
3-{(5-methyl-thiophen-2-ylmethyl)-[4-(3,3,5,5-tetramethyl-cyclohexyl)-thiazol-2-yl]-amino}-propionic acid tert-butyl ester (60 mg, 0.12 mmol) was treated with NaOH (2N NaOH: 1 mL; MeOH: 1 mL; THF: 1 mL) and the reaction was heated at 50° C. for 3 hrs following a method analogous to General Procedure G1 to produce 3-{(5-methyl-thiophen-2-ylmethyl)-[4-(3,3,5,5-tetramethyl-cyclohexyl)-thiazol-2-yl]-amino}-propionic acid (25 mg) after workup and purification. LC-MS m/z: 421 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 6.81 (d, 1H), 6.60 (d, 1H), 6.12 (s, 1H), 4.60 (S, 2H), 3.75-3.80 (m, 2H), 2.92 (m, 1H), 2.68-2.73 (m, 2H), 2.44 (s, 3H), 1.73 (d, 2H), 1.27-1.32 (m, 1H), 1.00-1.17 (m, 3H), 1.07 (s, 6H), 0.93 (s, 6H). The sodium carboxylate salt of the title compound could be prepared from this acid using a method analogous to General Procedure H.
Sources & evidence
- ORD record
- ord-38ae0f0b5dbb4578b59c62e2b5437677
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563742B2
Reaction notes
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