1,1'-Carbonyldiimidazole → tert-Butyl (S)-3-(6-tert-butoxycarbonylaminopyridin-3-yl)-2-[3-((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-11-yl)ureido]propionate

HRID 2274549ノート

反応式

HRID 2274549 の反応式
[NH2:1][C@@H:2]1[CH2:16][C:15]2=[CH:17][N:12]([CH:13]=[N:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][C@H:5]([CH:18]([CH3:20])[CH3:19])[NH:4][C:3]1=[O:21].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[NH2:34][C@@H:35]([CH2:43][C:44]1[CH:45]=[N:46][C:47]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[CH:48][CH:49]=1)[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>CN(C=O)C>[C:54]([O:53][C:51]([NH:50][C:47]1[N:46]=[CH:45][C:44]([CH2:43][C@H:35]([NH:34][C:22]([NH:1][C@@H:2]2[CH2:16][C:15]3=[CH:17][N:12]([CH:13]=[N:14]3)[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][C@H:5]([CH:18]([CH3:19])[CH3:20])[NH:4][C:3]2=[O:21])=[O:23])[C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[CH:49][CH:48]=1)=[O:52])([CH3:57])([CH3:56])[CH3:55]

参加物

5

反応物 3

HCID 682631,1'-Carbonyldiimidazole2 回HCID 58360487tert-Butyl (S)-2-amino-3-(6-tert-butoxycarbonylaminopyridin-3-yl)propionateHCID 67028858(8S,11R)-11-Amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-one

生成物 1

HCID 86655970tert-Butyl (S)-3-(6-tert-butoxycarbonylaminopyridin-3-yl)-2-[3-((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-11-yl)ureido]propionate収率 21.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 56 mg (190 μmol) of (8S,11R)-11-amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-one from step D in 5 ml of DMF was cooled to 0° C. and, while stirring, 32 mg (194 μmol) of 1,1′-carbonyldiimidazole were added. The mixture was stirred for 30 min, and then 64 mg (190 μmol) of tert-butyl (S)-2-amino-3-(6-tert-butoxycarbonylaminopyridin-3-yl)propionate were added, and the mixture was warmed to RT. After standing overnight, the same amount of 1,1′-carbonyldiimidazole was again added, and the mixture was stirred for a further 24 h. It was then concentrated and purified by preparative HPLC. 27 mg of the desired compound were obtained.

後処理

  1. stirringThe mixture was stirred for 30 min
  2. stirringthe mixture was stirred for a further 24 h
  3. concentrationIt was then concentrated
  4. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-7a7197315229446dadb0d0b4cff55fa8
出典データセット
uspto-grants-2015_09
特許番号
US09126955B2

反応ノート

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