1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-trityl-amino-ethyl)-4-ethynyl-benzamide
Reaction equation
O[C@H](C)[C@H](NC([C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)=[CH:13][CH:12]=1)=O)C(OC)=O.CCN=C=NCCCN(C)C.[CH:37]1[CH:38]=[CH:39][C:40]2N(O)N=N[C:41]=2[CH:42]=1.COC(=O)[CH:50]([NH:60][C:61](=[O:79])[C:62]1[CH:67]=[CH:66][C:65]([C:68]#[C:69]C#CC2C=CC(N)=CC=2)=[CH:64][CH:63]=1)[CH2:51][NH:52]C(OC(C)(C)C)=O.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:17]([CH:51]([NH2:52])[CH2:50][NH:60][C:61](=[O:79])[C:62]1[CH:67]=[CH:66][C:65]([C:68]#[CH:69])=[CH:64][CH:63]=1)([C:14]1[CH:13]=[CH:12][CH:11]=[CH:16][CH:15]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:42]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1Participants
8
Reactant 5
HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide
HCID 757711-Hydroxybenzotriazole
HCID 81531Diisopropylethylamine
HCID 578970282-{4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoylamino}-3-tert-butoxycarbonylamino-propionic acid methyl ester
HCID 59697585methyl(2S,3R)-3-hydroxy-2-{[4-(phenylcarbonyl)phenyl]carbonylamino}butanoateProduct 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-ethynylbenzoic acid 1 (292 mg, 2.00 mmol), EDCI (382 mg, 2.00 mmol), and HOBt (270 mg, 2.00 mmol) in DMF (10 mL) was added N-trityl ethylenediamine 2 (810 mg, 2.67 mmol) and DIEA (1.4 mL, 8.0 mmol). The reaction mixture was stirred 24 h, diluted with EtOAc (200 mL), washed with 0.5 M HCl (60 mL), saturated NaHCO3 (2×60 mL), H2O (4×60 mL), dried over MgSO4 and concentrated to give 836 mg (97% yield) of N-(2-trityl-amino-ethyl)-4-ethynyl-benzamide 3 as a white solid, mp 50-51° C. Rf=0.40 (1:1 Hexanes/EtOAc).
Workup
- washwashed with 0.5 M HCl (60 mL), saturated NaHCO3 (2×60 mL), H2O (4×60 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-50edac234ba84a51af5826db7b41b824
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153843B2
Reaction notes
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