Triethylamine → acetic acid {[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl ester

HRID 1013602

반응식

HRID 1013602 반응식
Cl.[F:2][C:3]1[CH:4]=[C:5]([S:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]([CH2:22][NH2:23])[CH2:17][CH2:16][CH2:15]3)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[O:41]=[C:42](C)[CH2:43][O:44][C:45](=[O:47])[CH3:46]>C(Cl)Cl>[F:2][C:3]1[CH:4]=[C:5]([S:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:22][NH:23][C:42]([CH2:43][O:44][C:45](=[O:47])[CH3:46])=[O:41])[CH2:17][CH2:16][CH2:15]3)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 11593AcetoxyacetoneHCID 757711-HydroxybenzotriazoleHCID 66651558C-[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-methylamine hydrochloride

생성물 1

HCID 59207182acetic acid {[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl ester수율 70.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

C-[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-methylamine hydrochloride (0.12 gms, 0.338 mmole), 1-hydroxybenzotriazol (0.07 g, 0.507 mmol) ethylcarbodiimide (0.10 g, 0.507 mmol), triethylamine (0.3 mL, 2.0 mmol) and acetic acid 2-oxo-propyl ester (0.05 g, 0.40 mmol) were dissolved in 10 mL methylene chloride. The reaction mixture was stirred at room temperature for 24 hours. The reaction was quenched with water, and the entire mixture was absorbed on to silica gel and medium pressure chromatography, and eluted with ethyl acetate/hexanes (3:1) to give 0.1 g of acetic acid {[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl ester.

후처리

  1. customThe reaction was quenched with water
  2. customthe entire mixture was absorbed on to silica gel and medium pressure chromatography
  3. washeluted with ethyl acetate/hexanes (3:1)

출처 및 근거

ORD 기록
ord-53a5d1106e984c99b3437b32f9f5895b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981923B2

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