Potassium Carbonate → {4-[4-(2-{Benzyl-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]amino}-ethoxy)phenyl]butyl}carbamic acid benzyl ester

HRID 1696831ノート

反応式

HRID 1696831 の反応式
[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([OH:50])[CH2:48]Br)=[CH:43][C:42]=1[NH:51][CH:52]=[O:53])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:48][C@@H:47]([C:44]2[CH:45]=[CH:46][C:41]([O:40][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[C:42]([NH:51][CH:52]=[O:53])[CH:43]=2)[OH:50])=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11142645(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamideHCID 58100148{4-[4-(2-Benzylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

生成物 1

HCID 58100114{4-[4-(2-{Benzyl-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]amino}-ethoxy)phenyl]butyl}carbamic acid benzyl ester収率 50.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Benzylamine 16 (619 mg, 1.43 mmol) was added to a suspension of bromoalcohol 5 (500 mg, 1.43 mmol) and K2CO3 (495 mg, 3.58 mmol) methanol (10 mL) and tetrahydrofuran (5 mL). The suspension was stirred at ambient temperature for 15 h, then heated to 55° C. for 75 h. The solid was vacuum filtered and the filtrate was concentrated under vacuum. The resulting oil was subjected to column chromatography eluting with 5-50% ethyl acetate in hexanes to afford the desired product 17 (508 mg, 5%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 1.45-1.62 (m, 4H), 2.54 (t, 2H), 2.65-2.71 (m, 1H), 3.14-3.23 (m, 3H), 3.58-3.74 (m, 1H), 3.88-4.09 (m, 3H), 4.71 (br, 2H), 5.04-5.21 (m, 4H), 6.79-7.25 (m, 6H), 7.34-7.52 (m, 16H), 7.65-7.87 (m, 1H), 8.32-8.49 (m, 1H); m/z, (ESI) 702 [C43H47N3O6+H]+.

後処理

  1. temperatureheated to 55° C. for 75 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washeluting with 5-50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-1636d5e5f75a4ebf8019bf4e16a1255f
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

読み込み中…