1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2,4-dichloro-phenoxymethylsulfanyl)-N-(5-hydroxy-adamantan-2-yl)-N-methyl-acetamide
Reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][S:6][CH2:7][C:8]([OH:10])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[CH3:46][NH:47][CH:48]1[CH:55]2[CH2:56][C:51]3([OH:58])[CH2:52][CH:53]([CH2:57][CH:49]1[CH2:50]3)[CH2:54]2>C1COCC1>[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][S:6][CH2:7][C:8]([N:47]([CH:48]1[CH:55]2[CH2:54][CH:53]3[CH2:52][C:51]([OH:58])([CH2:50][CH:49]1[CH2:57]3)[CH2:56]2)[CH3:46])=[O:10]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of (2,4-dichloro-phenoxymethylsulfanyl)-acetic acid (125 mg, 0.47 mmol) in dry THF (20 mL) was added HOBt (76 mg, 0.56 mmol) and EDAC (108 mg, 0.56 mmol). After stirring for 1 hr at room temperature, DIPEA (180 μL) and 4-methylaminoadamantan-1-ol (93 mg, 0.52 mmol) were added and the resulting mixture was stirred for 16 hrs. at room temperature. The volatiles were removed in vacuo and the residue was purified using prep. HPLC/MS affording crude 2-(2,4-dichloro-phenoxymethylsulfanyl)-N-(5-hydroxy-adamantan-2-yl)-N-methyl-acetamide which was used without further purification in the next step.
Workup
- stirringthe resulting mixture was stirred for 16 hrs
- customat room temperature
- customThe volatiles were removed in vacuo
- customthe residue was purified
Sources & evidence
- ORD record
- ord-6f3f7b0d3371495aa5c2b77055cb1e88
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383683B2
Reaction notes
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