Tetrahydrofuran → HCID 131723246, compound

HRID 2184951Notes

Reaction equation

HRID 2184951 reaction equation
[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]CC)=O)=[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.[O:59]1[CH2:63][CH2:62]CC1>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][C:44](=[C:45]=[O:47])[O:59][CH2:63][CH3:62])=[CH:39][CH:40]=3)[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[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

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 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

Product 1

HCID 131723246HCID 131723246, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

892 mg (5.5 mmol) of carbonyldiimidazole (CDI) 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 tert-butyl (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).

Workup

  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

Sources & evidence

ORD record
ord-6586632c56f3442199fe9dc93fb3dbd4
Source dataset
uspto-grants-2002_06
Patent number
US06399620B1

Reaction notes

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