Reaktion #835192

ord-5d56a53571f94550bb379b842accdd8b

Reaktionsgleichung

Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
6b
Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
(+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic acid
CCOC(C)=O
Ethyl acetate
Cl
HCl
Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
6b
Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
(+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic acid
→
COc1ccc(-c2nc(CO[C@@H]3CCC[C@H](OCc4cccc(C)c4C(=O)O)C3)co2)cc1
7b
COc1ccc(-c2nc(CO[C@@H]3CCC[C@H](OCc4cccc(C)c4C(=O)O)C3)co2)cc1
cis-2-(3-(2-(4-Methoxyphenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic acid

Edukte

Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
6b
Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
(+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic acid
CCOC(C)=O
Ethyl acetate
Cl
HCl
Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
6b
Cc1cccc(CO[C@H]2CCC[C@@H](OCc3coc(-c4ccc(F)cc4)n3)C2)c1C(=O)O
(+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic acid

Reagenzien

Keine

Lösungsmittel

CO.C[O-].[Na+]
NaOMe MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

170 mg (0.39 mmol) of 6b were heated in 4 ml of 5.6 M NaOMe/MeOH solution at an oil bath temperature of 120° C. for 20 hours. Ethyl acetate and 2 N HCl were added, and the mixture was then worked up analogously to the synthesis of 6b. This gave 7b as a colorless amorphous solid. TLC: (methylene chloride/methanol/conc. ammonia, 30/5/1). Rf˜0.3. C26H29NO6 (451.52) MS(ESI): 452 (M+H+).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07399777B2uspto-grants-2008_07