Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate

HRID 324595

反応式

HRID 324595 の反応式
[OH:1][CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].Cl.[NH2:26][C@@H:27]([CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(N(C(C)C)CC)(C)C>C1COCC1>[C:3]12([CH2:2][O:1][C:13]([NH:26][C@@H:27]([CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])=[O:14])[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2

参加物

6

反応物 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 86585733(S)-tert-Butyl 2-amino-3-((tert-butoxycarbonyl)amino)propanoate hydrochloride

生成物 1

HCID 68828668tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of 10.9 g (65.4 mmol) of (1-hydroxymethyl)adamantane and 10.6 g (65.4 mmol) of carbonyldiimidazole in 60 ml of THF is stirred at 50° C. for 1.5 h. 9.7 g (32.7 mmol) of (13.9) in 25 ml of THF and 5.6 ml (32.7 mmol) of diisopropylethylamine (DIPEA) are added and the mixture is stirred at 60° C. for 4 h and then left to stand at room temperature overnight. The solvent is removed in vacuo and the residue is chromatographed through silica gel using heptane/ethyl acetate=7/3. 8.7 9 (59%) of (13.10) are obtained as a colorless oil.

後処理

  1. waitleft
  2. waitto stand at room temperature overnight
  3. customThe solvent is removed in vacuo
  4. customthe residue is chromatographed through silica gel

出典と根拠

ORDレコード
ord-792933421eae4e7fbca11c9b232f95ea
出典データセット
uspto-grants-2001_04
特許番号
US06218415B1

関連ノート

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