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 2040002ノート

反応式

HRID 2040002 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7e0f46dbe4aa48639fae20aeb0c53f53
出典データセット
uspto-grants-2013_11
特許番号
US08580777B2

反応ノート

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