Potassium Carbonate → [4-(4-{4-[2-(4-Benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethylamino]pentyl}-phenyl)butyl]carbamic acid benzyl ester

HRID 1696836ノート

反応式

HRID 1696836 の反応式
[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([NH2:26])[CH3:25])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:35][C:36]1[CH:41]=[CH:40][C:39]([C@@H:42]([OH:45])[CH2:43]Br)=[CH:38][C:37]=1[NH:46][CH:47]=[O:48])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([NH:26][CH2:43][C@@H:42]([C:39]2[CH:40]=[CH:41][C:36]([O:35][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[C:37]([NH:46][CH:47]=[O:48])[CH:38]=2)[OH:45])[CH3:25])=[CH:17][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11142645(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamideHCID 58100158{4-[4-(4-Aminopentyl)phenyl]butyl}carbamic acid benzyl ester

生成物 1

HCID 86649686[4-(4-{4-[2-(4-Benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethylamino]pentyl}-phenyl)butyl]carbamic acid benzyl ester

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A suspension composed of compound 26 (0.59 g, 1.60 mmol), compound 5 (0.42 g, 1.19 mmol); K2CO3 (0.23 g, 1.68 mmol) and chloroform (25 mL) was heated to reflux for 72 h, then cooled to ambient temperature. The solid was vacuum filtered and washed with chloroform (3×10 mL). The filtrate and the washings were combined and concentrated. The residue was subjected to column chromatography eluting with 0-10% methanol in dichloromethane. The un-reacted starting material 26 (0.39 g; 66% recovery) was recovered in the separation. A mixture of two diastereomers of the desired products 27, which were not separable in this step, was obtained (0.29 g, 28%) as a colorless, viscous oil: 1H NMR (500 MHz, CDCl3) δ 1.08 (d, 3H), 1.37 (m, 2H), 1.48-1.68 (m, 6H), 2.55 (m, 4H), 2.74 (br, 2H), 2.92 (m, 1H), 3.18 (m, 2H), 3.58 (m, 1H), 3.72 (m, 1H), 4.70 (m, 1H), 4.80 (br, 1H), 5.08 (m, 4H), 6.92 (m, 1H), 7.08 (m, 5H), 7.22 (t, 1H), 7.34 (m, 10H), 7.92 (s, 1H), 8.31 (s, 1H); m/z (ESI) 638 [C39H47N3O5+H]+.

後処理

  1. temperatureto reflux for 72 h
  2. filtrationfiltered
  3. washwashed with chloroform (3×10 mL)
  4. concentrationconcentrated
  5. washeluting with 0-10% methanol in dichloromethane
  6. customwas recovered in the separation
  7. additionA mixture of two diastereomers of the desired products 27, which
  8. customwas obtained (0.29 g, 28%) as a colorless, viscous oil

出典と根拠

ORDレコード
ord-01a5b76369b14de5a7354e365f319a1a
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

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