Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → tert-butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

HRID 1394013ノート

反応式

HRID 1394013 の反応式
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[OH:13][CH2:14][C:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.[NH2:25][C@@H:26]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:37][CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(N(C(C)C)CC)(C)C>O1CCCC1.C(OCC)(=O)C>[C:15]12([CH2:14][O:13][C:1]([NH:25][C@@H:26]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([O:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:39][CH:40]=3)[C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])=[O:2])[CH2:24][CH:19]3[CH2:18][CH:17]([CH2:23][CH:21]([CH2:20]3)[CH2:22]1)[CH2:16]2

参加物

7

反応物 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

生成物 1

HCID 15512209tert-butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate収率 85.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

892 mg (5.5 mmol) of carbonyldiimidazole (CDl) were added to a solution of 830 mg (5 mmol) of 1-hydroxymethyladamantane in 10 ml of tetrahydrofuran and the mixture was stirred overnight at RT. It was then treated with 1 g (2.57 mmol) of tertbutyl (2S)-2-amino-3-(4-(3-ethoxycarbonyl-propyloxy)phenyl)propionate and 442 μl (2.57 mmol) of diisopropylethylamine (DIPEA) and the mixture was stirred overnight at 50° C. After cooling, it was taken up in ethyl acetate and the organic phase was washed successively with 3% strength citric acid solution, sodium hydrogencarbonate solution, 3×H2O and saturated NaCl solution. The organic phase was dried using MgSO4, the drying agent was filtered off and the filtrate was concentrated. The residue was chromatographed on silica gel using CH2Cl2/CH3OH (99/1). 1.19 g (85%) of an oil were obtained, which was employed without further purification for the synthesis of (4.4).

後処理

  1. stirringthe mixture was stirred overnight at 50° C
  2. temperatureAfter cooling
  3. washthe organic phase was washed successively with 3% strength citric acid solution, sodium hydrogencarbonate solution, 3×H2O and saturated NaCl solution
  4. customThe organic phase was dried
  5. filtrationthe drying agent was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-03567993797f48239c8349d4d635abde
出典データセット
uspto-grants-2008_03
特許番号
US07348333B2

反応ノート

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