تفاعل #86664

معادلة التفاعل

EtOAc

DIBAL

Ester

(9R,12S,15S)-15-(4-Fluoro-benzenesulfonylamino)-12-isopropyl-11,14-dioxo-2-oxa-7-thia-10,13-diaza-bicyclo[15.2.2]henicosa-1(20),17(21),18-triene-9-carboxylic acid methyl ester

→

4-Fluoro-N-((9R,12S,15S)-9-formyl-12-isopropyl-11,14-dioxo-2-oxa-7-thia-10,13-diaza-bicyclo[15.2.2]henicosa-1(20),17(21), 18-trien-15-yl)-benzenesulfonamide

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to rt overnight
2. 2
   أخرىThe reaction mixture was partitioned between EtOAc and 1M hydrochloric acid
3. 3
   استخلاصThe aqueous phase was extracted again with EtOAc
4. 4
   تجفيفthe combined organic extracts were dried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىPurification
8. 8
   غسيلeluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc
9. 9
   أخرىto yield a light brown solid, 9 mg, 20%

الإجراء التجريبي

Ester 57 (47 mg) was dissolved in DCM (6 mL) under an atmosphere of argon. The reaction was cooled to −78° C. To the resultant solution DIBAL (0.42 mL) was added dropwise. This was stirred for 2 h before being allowed to warm to rt overnight. The reaction mixture was partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted again with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc to yield a light brown solid, 9 mg, 20%. Rf=0.45 (1/1 EtOAc/(50/70) petroleum ether).

المصدر