Analyzing the synthesis route of Ethyl 6-hydroxyhexanoate

The chemical industry reduces the impact on the environment during synthesis 5299-60-5, I believe this compound will play a more active role in future production and life.

Related Products of 5299-60-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.5299-60-5, name is Ethyl 6-hydroxyhexanoate, molecular formula is C8H16O3, molecular weight is 160.21, as common compound, the synthetic route is as follows.

To an oven-dried 3-necked 10 mL round-bottom flask under nitrogen was added l-cyclopentyl-3-(2-(4-hydroxyphenyl)-l,l-bis(3- (trifluoromethoxy)phenyl)ethyl)urea, prepared as described in Procedure 11, 6, 2 and 59, (50 mg, 0.1 mmol ), triphenylphosphine (34 mg, 0.1 mmol), ethyl 6- hydroxyhexanoate (17 mg, 0.1 mmol ) and dry THF (0.5 mL ). The reaction mixture was cooled in an ice-methanol bath and diethylazodicarboxylate ( 23 mg, 0.13 mmol ) was added via syringe. The reaction was allowed to warm to rt and stirred overnight. The reaction mixture was concentrated in vacuo and purified by ISCO silica gel chromatography using a gradient of 5-25% EtOAc / hexanes as eluent to yield ethyl 6-(4-(2-(3-cyclopentylureido)-2,2-bis(3-(trifluoromethoxy)phenyl)ethyl)phenoxy)hexanoate (Example 313) was isolated as a white solid (43 mg, 61% yield). HPLC: RT = 4.69 minutes ( Phenomenex Luna C18 5mu column 4.6 x 50 mm eluting with 10-90% aqueous methanol containing 0.1% phosphoric acid over a 4 minute gradient monitoring at 220 nni). LC/MS [M+H] 711.3 ( Phenomenex Luna C18 5mu column 4.6 x 30 mm eluting with 10-90% aqueous methanol containing 0.1% TFA over a 4 minute gradient monitoring at 220 nm). 1H NMR (400MHz , CDCl3) delta ppm 7.33 (t, J= 7.9 Hz, 2 H), 7.20 (d, J= 7.9 Hz, 2 H), 7.12 (d, J= 7.9 Hz, 2 H), 7.07 (s, 2 H), 6.62 (d, J= 8.8 Hz, 2 H), 6.56 (d, J= 8.8 Hz, 2 H), 4.10 (q, J= 7.1 Hz, 2 H), 3.86 t, J = 6.1Hz, 2 H), 3.68 (s, 1 H), 3.62 (t, J= 6.6Hz, 1 H), 2.30-2.27 (m, 2 H), 1.82-1.14 (m, 17 H), 1.23 (t, J= 7.1Hz, 3 H).

The chemical industry reduces the impact on the environment during synthesis 5299-60-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/62308; (2007); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts