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Triethylamine → (9H-fluoren-9-yl)methyl (1R,2S)-1-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-ylcarbamoyl)-2-methylcyclopropylcarbamate

HRID 1772358
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HRID 1772358 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@:19]3([C:23](O)=[O:24])[CH2:21][C@@H:20]3[CH3:22])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:39][C:40]1[S:41][C:42]([CH3:55])=[C:43]([CH3:54])[C:44]=1[C:45]([C:47]1[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=1)=[O:46]>CN(C=O)C.C(Cl)Cl>[Cl:53][C:50]1[CH:51]=[CH:52][C:47]([C:45]([C:44]2[C:43]([CH3:54])=[C:42]([CH3:55])[S:41][C:40]=2[NH:39][C:23]([C@@:19]2([NH:18][C:16](=[O:17])[O:15][CH2:14][CH:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[CH2:21][C@@H:20]2[CH3:22])=[O:24])=[O:46])=[CH:48][CH:49]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 719710(2-Amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanoneHCID 67951127(1R,2S)-1-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-methylcyclopropanecarboxylic acid

생성물 1

HCID 86706924(9H-fluoren-9-yl)methyl (1R,2S)-1-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-ylcarbamoyl)-2-methylcyclopropylcarbamate
수율 38.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

A round bottomed flask was charged with (1R,2S)-1-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-methylcyclopropanecarboxylic acid (408 mg, 1.209 mmol) and a stir bar. DCM (25 mL, 0.05 M) was added, followed by one drop of DMF and oxalyl chloride (97 μl, 1.109 mmol). Stirred at room temperature 1 h. A solution of triethylamine (562 μl, 4.03 mmol) and (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (268 mg, 1.008 mmol) in DCM (10 mL, 0.1 M) was added dropwise, and the solution stirred at room temperature overnight before being concentrated with celite and purified by flash chromatography to give (9H-fluoren-9-yl)methyl (1R,2S)-1-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-ylcarbamoyl)-2-methylcyclopropylcarbamate as a yellow amorphous solid (225 mg) LRMS (M+H)+: 586 m/z.

후처리

  1. stirringthe solution stirred at room temperature overnight
  2. concentrationbefore being concentrated with celite
  3. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-7b9add966bc7464d9132678cd8ec6d2a
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249161B2

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