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Method of svnthesising A.25Sodium hydride (60 %; 1.40 g, 36.0 mmol) is placed in DMF (70 mL), mixed with carboxylic acid ester A.a.1 (5.00 g, 32.0 mmol) and stirred for 45 min at 20C. Then benzylbromide A.b.1 (4.10 mL, 32.0 mmol) is metered in and the mixture is stirred for a further 3 h at 20C. The reaction mixture is combined with HCI (50 mL, 1 N) and DCM (50 mL), the organic phase is separated off and extracted again with HCI (2 x 30 mL). Then the organic phase is dried, the solvent is eliminated in vacuo and carboxylic acid ester A*.25 (10.0 g, 89 %; HPLC-MS: MS(M+H)+ = 281 ; tRel = 1 .57 min; method FEC3) is obtained.
89%
Sodium hydride (60 %; 1.40 g, 36.0 mmol) is placed in DMF (70 mL), carboxylic acid ester A.a.1 (5.00 g, 32.0 mmol) is added and the mixture is stirred for 45 min at 20C. Then benzylbromide A.b.1 (4.10 mL, 32.0 mmol) is metered in and the mixture is stirred for a further 3 h at 20C. The reaction mixture is combined with HCI (50 mL, 1 N) and DCM (50 mL), the organic phase is separated off and extracted again with HCI (2 x 30 mL). Then the organic phase is dried, the solvent is eliminated in vacuo and carboxylic acid ester A*.32 (10.0 g, 89 %; HPLC-MS: MS(M+H)+ = 281 ; = 1.57 min; method FEC3) is obtained.
89%
Method of Synthesising A.25Sodium hydride (60%; 1.40 g, 36.0 mmol) is placed in DMF (70 mL), mixed with carboxylic acid ester A.a.1 (5.00 g, 32.0 mmol) and stirred for 45 min at 20 C. Then benzylbromide A.b.1 (4.10 mL, 32.0 mmol) is metered in and the mixture is stirred for a further 3 h at 20 C. The reaction mixture is combined with HCl (50 mL, 1 N) and DCM (50 mL), the organic phase is separated off and extracted again with HCl (2×30 mL). Then the organic phase is dried, the solvent is eliminated in vacuo and carboxylic acid ester A*.25 (10.0 g, 89%; HPLC-MS: MS (M+H)+=281; tRet.=1.57 min; method FEC3) is obtained.Carboxylic acid ester A*.25 (1.9 g, 5.6 mmol) is taken up in MeOH (7.3 mL) and mixed with NaOH (6.2 mL, 1 M). After 16 h at 20 C. the mixture is diluted with water and extracted with DCM. The organic phase is discarded, the aqueous phase is acidified and extracted with DCM. The organic phase is dried on Na2SO4, filtered, the solvent is eliminated in vacuo and the free carboxylic acid A.25 (694 mg, 47%; HPLC-MS: MS (M+H)+=267; tRet.=0.29 min; method FECB4) is obtained.
a) Synthesis of free cyclic carboxylic acids A.1; Method for svnthesising A. Ia; Sodium hydride (60 %; 28.6 mg, 0.714 mmol) is suspended in 1.5 rnL DMF, combined with carboxylic acid ester B.l-la (100 mg, 0.649 mmol) and stirred for 45 min at 20C. Benzyl bromide B.2a (134 mg, 0.649 mmol) is metered into the suspension and it is stirred for a further 3 h at 200C. The reaction mixture is combined with 1 N hydrochloric acid and DCM, the organic phase is separated off and extracted 2 x with 1 N hydrochloric acid. Then the organic phase is dried, the solvent is eliminated in vacuo and carboxylic acid ester A.l*a (HPLC-MS: tRet. = 1.50 min; MS(M+H)+ = 281; method FECB3) is obtained.
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