Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester

White to off-white solid

b1 (6.96 g; 16.36 mmol; 1.00 eq.) was dissolved in DMF (139 ml). PyBOP (12.77 g; 24.54 mmol; 1.50 eq.) and DIPEA (14.25 ml; 81.79 mmol; 5.00 eq.) were added and stirred until dissolved completely. N-Boc-N-methyl-1, 3-diaminopropane hydrochloride b2 (4.04 g; 17.99 mmol; 1.10 eq.) was added and the reaction mixture was stirred at room temperature for 15 min. Complete conversion to the product was observed by LCMS. The reaction mixture was diluted with 400 ml of dichloromethane and was washed three times with 400 ml of 0.1 N HCl. The organic layer was washed three times with 400 ml of saturated NaHCO3solution and once with 200 ml of brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was dissolved in 14 ml of dichloromethane and purified by normal phase flash chromatography. The product containing fractions were pooled and the solvent was evaporated. The final material was dried under high vacuum to yield amide compound b3 as a white foam. Yield: 8.81 g (14.79 mmol, 90%).(225 mg, 0.529 rnmol) was dissolved in DMF (3 mL) and Sa(300 rng, 0.847 mmol), HATU (201 mg, 0.529 mrnoi), and collidine (0.48 rnL, 3.70 mrnol)were added. The mixture was stirred at RT for 2 h to yield Sb. For fmoc deprotection, piperidine (0.22 mL, 2.16 mrnol) was added and stirring was continued for 1 h. Acetic acid (1rnL) was added, and Sc was purified by RP-HLPC.Yield: 285 mg (0.436 mmol as TFA salt)MS: m/z 562.54 = [M+Naf, (calculated = 562.67). (225 mg, 0.529 mmol) was dissolved in DMF (3 mL) and 7a (300 mg, 0.847 mmol), HATU (201 mg, 0.529 mmol), and collidine (0.48 mL, 3.70 mmol) were added. The mixture was stirred at RT for 2 h to yield 7b. For fmoc deprotection, piperidine (0.22 mL, 2.16 mmol) was added and stirring was continued for 1 h. Acetic acid (1 mL) was added, and 7c was purified by RP-HLPC. Yield: 285 mg (0.436 mmol as TFA salt) (0495) MS: m/z 562.54=[M+Na]+, (calculated=562.67). (225 mg, 0.529 mmol) was dissolved in DMF (3 mL) and 7a (300 mg, 0.847 mmol), HATU (201 mg, 0.529 mmol), and collidine (0.48 mL, 3.70 mmol) were added. The mixture was stirred at RT for 2 h to yield 7b (225 mg, 0.529 mmol) was dissolved inDMF (3 mL) and 7a (300 mg, 0.847 mmol), HATU (201 mg, 0.529 mmol), and collidine (0.48 mL, 3.70mmol) were added. The mixture was stirred at RT for 2 h to yield 7b. For fmoc deprotection, piperidine(0.22 mL, 2.16 mmol) was added and stirring was continued for 1 h. Acetic acid (1 mL) was added, and 7cwas purified by RP-HLPC. Yield: 285 mg (0.436 mmol as TFA salt), MS: m/z 562.54=[M+Na]+, (calculated=562.67).N-Fmoc-N-Me-Asp(OfBu)-OH (225 mg, 0.529 mmol) was dissolved in DMF (3 ml_) and 7a (300 mg, 0.847 mmol), FIATU (201 mg, 0.529 mmol), and collidine (0.48 ml_, 3.70 mmol) were added. The mixture was stirred at RT for 2 h to yield 7b. For fmoc deprotection, piperidine (0.22 ml_, 2.16 mmol) was added and stirring was continued for 1 h. Acetic acid (1 ml_) was added, and 7c was purified by RP-HLPC.Yield: 285 mg (0.436 mmol as TFA salt)MS: m/z 562.54 = [M+Na]+, (calculated = 562.67).

Molecular Weight:425.5
XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:9
Exact Mass:425.18383758
Monoisotopic Mass:425.18383758
Topological Polar Surface Area:93.1
Heavy Atom Count:31
Complexity:650
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes