Piperidine → (13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

HRID 2040002노트

반응식

HRID 2040002 반응식
[CH:1]([C@@H:4]1[NH:23][C:22](=[O:24])[C@H:21]([NH:25]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[CH2:20][C:19]2=[CH:43][CH:44]=[C:16]([CH:17]=[CH:18]2)[O:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2].N1CCCCC1>CO.[Pd]>[NH2:25][C@@H:21]1[CH2:20][C:19]2=[CH:18][CH:17]=[C:16]([CH:44]=[CH:43]2)[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C@H:4]([CH:1]([CH3:2])[CH3:3])[NH:23][C:22]1=[O:24]

참가 물질

5

반응물 2

HCID 8082PiperidineHCID 866559669H-Fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)carbamate

생성물 1

HCID 67028556(13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of 0.87 (1.46 mmol) of 9H-fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)-carbamate and 0.16 g of 10% Pd/C in 100 ml of methanol was stirred under a hydrogen atmosphere at RT. After stirring overnight and addition of 0.5 ml of piperidine, stirring was continued for 2 h, and the mixture was filtered and freed of solvent. The residue was separated by preparative HPLC. The required fractions were combined and freeze dried. 0.18 g of the title compound was obtained as trifluoroacetate.

후처리

  1. stirringAfter stirring overnight
  2. stirringstirring
  3. filtrationthe mixture was filtered
  4. customThe residue was separated by preparative HPLC
  5. customfreeze dried

출처 및 근거

ORD 기록
ord-7e0f46dbe4aa48639fae20aeb0c53f53
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580777B2

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