홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Ethylamine → (RS)-1-{(4-chlorophenyl)[4-(N-ethylcarbamoyl)phenyl]methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine

HRID 1058788
노트
인쇄 미리보기

반응식

HRID 1058788 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[N:11]2[CH2:14][C:13](=[C:15]([C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=3)[S:16]([CH3:19])(=[O:18])=[O:17])[CH2:12]2)=[CH:6][CH:5]=1)([OH:3])=O.Cl.C[NH:37][CH:38](N=C=NCC)[CH2:39]CNC.O.OC1C2N=NNC=2C=CC=1.C(N)C>C1COCC1.C(OCC)(=O)C.C1CCCCC1.ClCCl>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:1](=[O:3])[NH:37][CH2:38][CH3:39])=[CH:9][CH:8]=2)[N:11]2[CH2:14][C:13](=[C:15]([C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=3)[S:16]([CH3:19])(=[O:17])=[O:18])[CH2:12]2)=[CH:33][CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 6341EthylamineHCID 22565413(RS)-1-{(4-carboxyphenyl)(4-chlorophenyl)methyl]-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidineHCID 230638721,3-Dimethylaminopropyl-3-ethylcarbodiimide hydrochlorideHCID 178526939HCID 178526939, 화합물

생성물 1

HCID 10119284(RS)-1-{(4-chlorophenyl)[4-(N-ethylcarbamoyl)phenyl]methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine
수율 29.7%

시약·촉매·용매 4

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8078Cyclohexane용매HCID 8857Ethyl Acetate용매

실험 절차

The operation is carried out as in Example 52, starting with 1 g of (RS)-1-{(4-carboxyphenyl)-(4-chlorophenyl)methyl]-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine, 0.38 g of 1,3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride, 22 mg of hydroxybenzotriazole hydrate, 30 cm3 of dichloromethane and 0.83 cm3 of a 2 M ethylamine solution in THF, chromatographing on a silica gel column (particle size 0.04-0.06 mm, diameter 4.1 cm, height 15 cm), at an argon pressure of 0.5 bar with a mixture of ethyl acetate and cyclohexane (45/55 by volume) as eluent and collecting 30 cm3 fractions. Fractions 22 to 32 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 0.29 g of (RS)-1-{(4-chlorophenyl)[4-(N-ethylcarbamoyl)phenyl]methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine is obtained in the form of a white solid [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 1.07 (3H, t, J=6 Hz, CH3), 3.00 (3H, s, SCH3), 3.35 (2H, m, NCH2), 3.90 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.80 (1H, s, NCH), 7.15 (2H, d, J=8 Hz, 2CH arom.), 7.30 (1H, t, J=8 Hz, CH arom.), 7.35 (2H, d, J=7 Hz, 2CH arom.), 7.48 (4H, m, 4CH arom.), 7.74 (2H, d, J=7 Hz, 2CH arom.), 8.37 (1H, t, CONH)].

후처리

  1. customcollecting 30 cm3 fractions
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

출처 및 근거

ORD 기록
ord-77f9070eb7ab49348073f68d984093eb
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06518264B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트