Anisomycin → Deacetylanisomycin

반응식

C([O:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][NH:7][C@@H:6]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=O)C.N.CO>>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][C@@H:6]2[C@H:5]([OH:4])[C@@H:9]([OH:10])[CH2:8][NH:7]2)=[CH:17][CH:16]=1

참가 물질

반응물 2

HCID 253602Anisomycin

HCID 21705897Ammonia methanol

생성물 1

HCID 11790817Deacetylanisomycin

실험 절차

To a 500 mL round bottom flask containing solid (2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate (513.3 mg, 1.935 mmol) and a magnetic stir bar is added 2M NH3/MeOH (200 mL, 400 mmol). The resulting light tan solution is capped and stirred at room temp for 5 days. The solvent is removed in vacuo to give the title compound that is used directly “as is” in the next step. LC/MS (Condition A): ret. T=1.42 min, (M+H)+ 224.11.

후처리

customThe resulting light tan solution is capped
customThe solvent is removed in vacuo

출처 및 근거

ORD 기록: ord-785f9845e5f84015877756ae03d66b59
출처 데이터셋: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09169295B2

반응 노트

불러오는 중…