[N:1]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5]N1C(=O)CCC1=O)=O.N1(C(OC(C)(C)C)=O)[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25](O)=O.[NH2:38][C@H:39]([C:43]([OH:45])=[O:44])[C@@H](C)O.C([O-])(O)=O.[Na+].Cl.O1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>O>[N:1]1([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([NH:38][C@H:39]([C:43]([OH:45])=[O:44])[C@@H:54]([CH3:53])[O:55][CH2:56][C:57]1[CH:25]=[CH:24][CH:28]=[CH:29][CH:30]=1)=[O:5]Boc-Pro-Thr(OBzl)-OH was prepared by coupling Boc-Pro-OSu (the N-hydroxysuccinamide ester of Boc-Pro-OH) to H-Thr (OBzl) - OH. H-Thr (OBzl)-OH.HCL was dissolved in 25 ml of water, NaHCO3 (6.21 g, 73.9 mmoles) and a solution of Boc-Pro-Osu (5.07 g, 16.25 mmoles) in 25 ml of dioxane were added. After stirring 3 hours, the reaction mixture was acidified with hydrochloric acid and the product extracted into ethyl acetate. It was washed with 0.2N HCl prepared in saturated aqueous NaCl, saturated NaCl and dried over anhydrous Na2SO4. Solvent was evaporated to yield 6.24 g (mp 120°-12.5°).
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