H-GLU(OBZL)-OTBU HCL

White crystalline powder

Glutamic acid-5-benzyl ester (75 g) was added to 750 ml of t-butyl acetate, External ice water cooling, T <5 perchloric acid drop 26ml, plus complete, temperature T = 25 , L-glutamic acid-5-benzyl ester was completely treated by TLC; Sodium carbonate aqueous solution adjusted PH = 7-8, to the water layer, tert-butyl acetate layer, washed with water, brine, anhydrous sodium sulfate drying, filter desiccant, 50 ° C under vacuum distillation tert-butyl acetate, And the oily substance was diluted with a small amount of ether, to which a previously prepared ether hydrochloride was adjusted to pH = 4-5, the product was precipitated, Filtered and dried to obtain 90 g of the product L-glutamic acid-5-benzyl ester-1-t-butyl ester hydrochloride, The purity was 98.5percent and the final yield was 80percent.To a solution of DSC (1.73 g, 6.76 mmol) in DMF (31.6 ml), a, y-di-tertbutyl L-glutamate (2 g, 6.76 mmol) was added in portions at 0C. After 50 minutes, TEA (937 p1, 6.76 mmol) was added. After complete conversion, a-tert-butyl-y-benzyl L-glutamate (2.23 g, 6.76 mmol) and TEA (1.87 ml, 13.52 mmol) were added at 000. The reaction mixture was stirred overnight at room temperature. DMF was removed in vacuo and the residue was dissolved in MTBE (100 ml). The organic layer was washed with 15% citric acid solution (2x100 ml), water (2xlOOml), saturated NaHCO3 solution (2x1 00 ml) and water (80 ml) in sequence. The organic layer was dried over MgSO4, filtered and concentrated. The resulting yellowish oil was purified by chromatography on silica gel column (0-33% gradient of ethyl acetate (EtOAc) in hexane) to provide the urea HOP 30.21 75 as colorless syrup (3.02 g, 77%). MS (ESI+): m/zfound: 579.17 calc.: 579.72 [M+H] found: 601.35 calc.:601.70 [M-?-Na] found: 1180.35 calc.: 1180.41 [2M-?-Na].To a solution of DSC (1.73 g, 6.76 mmol) in DMF (31.6 ml), a, y-di-tertbutyl L-glutamate (2 g, 6.76 mmol) was added in portions at 0C. After 50 minutes, TEA (937 p1, 6.76 mmol) was added. After complete conversion, a-tert-butyl-y-benzyl L-glutamate (2.23 g, 6.76 mmol) and TEA (1.87 ml, 13.52 mmol) were added at 000. The reaction mixture was stirred overnight at room temperature. DMF was removed in vacuo and the residue was dissolved in MTBE (100 ml). The organic layer was washed with 15% citric acid solution (2x100 ml), water (2xlOOml), saturated NaHCO3 solution (2x1 00 ml) and water (80 ml) in sequence. The organic layer was dried over MgSO4, filtered and concentrated. The resulting yellowish oil was purified by chromatography on silica gel column (0-33% gradient of ethyl acetate (EtOAc) in hexane) to provide the urea HOP 30.21 75 as colorless syrup (3.02 g, 77%).[00153] MS (ESI+): m/zfound: 579.17 calc.: 579.72 [M+H] found: 601.35 calc.:601.70 [M-?-Na] found: 1180.35 calc.: 1180.41 [2M-?-Na].

Molecular Weight:329.82
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:9
Exact Mass:329.1393859
Monoisotopic Mass:329.1393859
Topological Polar Surface Area:78.6
Heavy Atom Count:22
Complexity:343
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes