2-Aminoimidazoline hydrochloride → tert-Butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-(4,5-dihydroimidazoi-2-ylcarbamoyl)propyloxy)phenyl)propionate

HRID 1394014Notes

Reaction equation

HRID 1394014 reaction equation
[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]CC)=O)=[CH:27][CH:26]=3)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.[NH2:41][C:42]1[NH:43][CH2:44][CH2:45][N:46]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35](=[O:37])[NH:41][C:42]4[NH:46][CH2:45][CH2:44][N:43]=4)=[CH:29][CH:30]=3)[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])=[O:14])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 127975392-Aminoimidazoline hydrochlorideHCID 15512209tert-butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67633290tert-Butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-(4,5-dihydroimidazoi-2-ylcarbamoyl)propyloxy)phenyl)propionateYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

436 mg (0.8 mmol) of tert-butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate were added to a solution of 388 mg (3.2 mmol) of 2-amino-4,5-dihydroimidazole hydrochloride and 359 mg (3.2 mmol) of potassium tert-butoxide in 10 ml of DMF. The mixture was stirred overnight. After the reaction had ended, it was worked up analogously to Example 4c and chromatographed on silica gel using the same eluent mixture. 188 mg (0.32 mmol) of (5.1) were obtained.

Workup

  1. customchromatographed on silica gel using the same eluent mixture

Sources & evidence

ORD record
ord-a855078ce9fb4a82b0be8273e7176e97
Source dataset
uspto-grants-2008_03
Patent number
US07348333B2

Reaction notes

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