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

HRID 1394013노트

반응식

HRID 1394013 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-03567993797f48239c8349d4d635abde
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348333B2

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