tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-{2-[3-(2-fluoroethoxy)phenyl]ethyl}pyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate → (3S)-3-(5-{2-[3-(2-fluoroethoxy)phenyl]ethyl}pyridin-3-yl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid

HRID 526365ノート

反応式

HRID 526365 の反応式
C([O:5][C:6](=[O:53])[CH2:7][C@H:8]([NH:27][C:28]([C@@H:30]1[CH2:35][CH2:34][CH2:33][N:32]([C:36](=[O:52])[CH2:37][CH2:38][CH:39]2[CH2:44][CH2:43][N:42](C(OC(C)(C)C)=O)[CH2:41][CH2:40]2)[CH2:31]1)=[O:29])[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][F:26])[CH:18]=2)[CH:14]=1)(C)(C)C>C(O)=O>[F:26][CH2:25][CH2:24][O:23][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][C:13]2[CH:14]=[C:9]([C@@H:8]([NH:27][C:28]([C@@H:30]3[CH2:35][CH2:34][CH2:33][N:32]([C:36](=[O:52])[CH2:37][CH2:38][CH:39]4[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]4)[CH2:31]3)=[O:29])[CH2:7][C:6]([OH:53])=[O:5])[CH:10]=[N:11][CH:12]=2)[CH:22]=[CH:21][CH:20]=1

参加物

3

反応物 1

HCID 89407743tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-{2-[3-(2-fluoroethoxy)phenyl]ethyl}pyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

生成物 1

HCID 71609498(3S)-3-(5-{2-[3-(2-fluoroethoxy)phenyl]ethyl}pyridin-3-yl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid収率 68.6%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

Tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-{2-[3-(2-fluoroethoxy)phenyl]ethyl}pyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (20 mg, 30 μmol) was heated to 60° C. in formic acid for 50 minutes. The solution was then concentrated in vacuum and the residue purified by preparative HPLC to yield 12 mg of (3S)-3-(5-{2-[3-(2-fluoroethoxy)phenyl]ethyl}pyridin-3-yl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid.

後処理

  1. concentrationThe solution was then concentrated in vacuum
  2. customthe residue purified by preparative HPLC

出典と根拠

ORDレコード
ord-c8410699d63d4cd797ff0032c1164d5d
出典データセット
uspto-grants-2016_05
特許番号
US09345793B2

反応ノート

読み込み中…