ChemicalBook CAS DataBase List Z-PRO-PRO-OH

Z-PRO-PRO-OH synthesis

6synthesis methods

Product Name:Z-PRO-PRO-OH
CAS Number:7360-23-8
Molecular formula:C18H22N2O5
Molecular Weight:346.38

L-Proline, 1-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester

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Yield:7360-23-8 86%

Reaction Conditions:

with water;lithium hydroxide in tetrahydrofuran at 20;

Steps:

4 Preparation of (S)-1-((S)-1-(Benzyloxycarbonyl) pyrrolidine-2-carbonyl) pyrrolidine-2-carboxylic Acid (Compound V)

To a mixture of THF (500 mL) and water (500 mL) was charged the solution of Compound IV in THF, obtained from Example 3.
Lithium Hydroxide (20.2 g, 0.48 moles) was added to the reaction mixture and stirred at room temperature overnight.
Reaction mixture was washed with MTBE and pH of aqueous layer was adjusted to 1.0-2.0 with concentrated HCl.
The resulting slurry was stirred for 1-2 hours at 0-5° C. and filtered.
The filter cake was washed with water and MTBE and then dried to obtain Compound V (122 g, 86%). ‘H-NMR (400 MHz, DMSO-d5): ? 7.39-7.25 (m, 5H), 5.08-4.88 (m, 2H), 4.53-4.49 (m, 1H), 4.24 (dq, 1H),3.70-3.64 (m, 1H), 3.57 (s, 3H), 3.55-3.38 (m, 3H), 2.27-1.66 (m, 8H).

References:

US2019/31715,2019,A1 Location in patent:Paragraph 0168; 0169