[NH2:1][C:2]1[S:3][C:4]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[C:5]([C:7]([N:9]2[C@H:14]([CH2:15][NH:16]C(=O)C(F)(F)F)[CH2:13][C@H:12]3[C@@H:10]2[CH2:11]3)=[O:8])[N:6]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].CC(OC)(C)C>CO.CCOC(C)=O>[NH2:16][CH2:15][C@@H:14]1[CH2:13][C@H:12]2[C@H:10]([CH2:11]2)[N:9]1[C:7]([C:5]1[N:6]=[C:2]([NH2:1])[S:3][C:4]=1[C:23]1[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=1)=[O:8]
A solution of N-[(1S,3S,5S)-2-(2-amino-5-m-tolyl-thiazole-4-carbonyl)-2-aza-bicyclo[3.1.0]hex-3-ylmethyl]-2,2,2-trifluoro-acetamide (2.33 mmol) in MeOH (7.7 mL) is treated with a sat. aqueous K2CO3 solution (0.62 mL) and stirred at 60° C. for 5 h. After stirring for additional 16 h at RT the mixture is made basic by slow addition of aqueous NaOH solution (32%). Equal volumes of TBME and EtOAc are added and the mixture is stirred vigorously for 1 h. The layers are separated, the aqueous layer is extracted with a mixture of TBME and EtOAc and the combined organic layers are dried over Na2SO4. The solvents are removed in vacuo to give the desired product which is used without further purification. LC-MS (basic): tR=0.67 min; [M+H]+=329.0.
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