1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl (2S,3R)-3-hydroxy-1-phenyl-4-(5-(prop-1-en-2-yl)nicotinamido)butan-2-ylcarbamate
Reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=O)[CH3:3].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:34][CH2:35][C@@H:36]([OH:53])[C@@H:37]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CCN(C(C)C)C(C)C>ClCCl>[OH:53][C@H:36]([CH2:35][NH:34][C:9](=[O:11])[C:8]1[CH:12]=[C:4]([C:2]([CH3:3])=[CH2:1])[CH:5]=[N:6][CH:7]=1)[C@@H:37]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:49])[CH3:50])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To 5-(prop-1-en-2-yl)nicotinic acid (200 mg, 1.23 mmol) in dichlormethane (10 ml) at rt, EDCI (330 mg, 1.72 mmol) and HOBT (200 mg, 1.48 mmol) were added. After stirring at rt for 10 minutes, tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate (344 mg, 1.23 mmol) was added followed by DIPEA (0.2 ml). After stirring overnight at rt, reaction mixture was worked up as usual and residue was column purified (90% ethylacetate/10% hexanes) to yield 280 mg of tert-butyl (2S,3R)-3-hydroxy-1-phenyl-4-(5-(prop-1-en-2-yl)nicotinamido)butan-2-ylcarbamate, which on stirring with 4N HCl in dioxane for 4 h yields the HCl salt of N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-5-(prop-1-en-2-yl)nicotinamide.
Workup
- stirringAfter stirring overnight at rt
- customreaction mixture
- custompurified (90% ethylacetate/10% hexanes)
Sources & evidence
- ORD record
- ord-18eb0325680e4480bfc472267b5c7856
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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