2-(Dimethylamino)ethanol → Tert-butyl 3-(3-((2-(dimethylamino)ethoxy)carbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 1750947Notes

Reaction equation

HRID 1750947 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:34][CH2:33][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][N:13]([CH2:22][C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=[O:27])[C:12]2=[O:32])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53]O>CN(C)C1C=CN=CC=1.ClCCl>[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53][O:27][C:26]([C:25]1[CH:24]=[C:23]([CH:31]=[CH:30][CH:29]=1)[CH2:22][N:13]1[C:12](=[O:32])[C:11]2([CH2:33][CH2:34][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14]1)=[O:28]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 10868DicyclohexylcarbodiimideHCID 666520763-((8-(Tert-butoxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Product 1

HCID 58046654Tert-butyl 3-(3-((2-(dimethylamino)ethoxy)carbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylateYield 43.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((8-(tert-butoxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid (0.34 g, 0.73 mmol), dicyclohexylcarbodiimide (0.18 g, 0.88 mmol) and 4-(dimethylamino)pyridine (0.011 g, 0.088 mmol) in dichloromethane (10 mL), was added N,N-dimethylethanolamine (0.065 mg, 0.73 mmol). After stirring at room temperature for 60 hours, the reaction mixture was filtered, concentrated in vacuo and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain tert-butyl 3-(3-((2-(dimethylamino)ethoxy)carbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.17 g, 43%); MS for C30H40N4O5 m/z 537 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customisolated by preparatory TLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-eba553daf2aa4950b41c99e57e8dc80c
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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