tert-butyl 4-{3-[(3R)-3-({(1S)-1-[5-(benzyloxy)pyridin-3-yl]-3-tert-butoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate → Tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-hydroxypyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

HRID 526376ノート

反応式

HRID 526376 の反応式
C([O:8][C:9]1[CH:10]=[C:11]([C@@H:15]([NH:24][C:25]([C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33](=[O:49])[CH2:34][CH2:35][CH:36]3[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]3)[CH2:28]2)=[O:26])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[N:13][CH:14]=1)C1C=CC=CC=1>C(OCC)(=O)C.CO.[Pd]>[C:20]([O:19][C:17](=[O:18])[CH2:16][C@H:15]([NH:24][C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33](=[O:49])[CH2:34][CH2:35][CH:36]2[CH2:37][CH2:38][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40][CH2:41]2)[CH2:28]1)=[O:26])[C:11]1[CH:12]=[N:13][CH:14]=[C:9]([OH:8])[CH:10]=1)([CH3:21])([CH3:23])[CH3:22]

参加物

5

反応物 1

HCID 71258943tert-butyl 4-{3-[(3R)-3-({(1S)-1-[5-(benzyloxy)pyridin-3-yl]-3-tert-butoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

生成物 1

HCID 71259825Tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-hydroxypyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate収率 93.5%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Tert-butyl 4-{3-[(3R)-3-({(1S)-1-[5-(benzyloxy)pyridin-3-yl]-3-tert-butoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (1.69 g, 2.49 mmol) in ethyl acetate (73 mL) and methanol (12 mL) was stirred for 20 hours at room temperature under a hydrogen atmosphere in the presence of palladium on charcoal (10%, 170 mg). The suspension was filtrated through celite, which were washed thoroughly with methanol. The solution was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (methanol in ethyl acetate 0 to 15%) to yield 1.37 g of Tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-hydroxypyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate.

後処理

  1. filtrationThe suspension was filtrated through celite, which
  2. washwere washed thoroughly with methanol
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe residue was purified by chromatography on silica gel (methanol in ethyl acetate 0 to 15%)

出典と根拠

ORDレコード
ord-a5a6a8ec653e4a20a288b096fc38902b
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…