1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2,4-dichloro-phenoxymethylsulfanyl)-N-(5-hydroxy-adamantan-2-yl)-N-methyl-acetamide

HRID 390790노트

반응식

HRID 390790 반응식
[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]

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 37214804-(Methylamino)adamantan-1-olHCID 68579334(2,4-Dichloro-phenoxymethylsulfanyl)-acetic acid

생성물 1

HCID 685801542-(2,4-dichloro-phenoxymethylsulfanyl)-N-(5-hydroxy-adamantan-2-yl)-N-methyl-acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. stirringthe resulting mixture was stirred for 16 hrs
  2. customat room temperature
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified

출처 및 근거

ORD 기록
ord-6f3f7b0d3371495aa5c2b77055cb1e88
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383683B2

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