Ethanol → propan-2-yl 2-methyl-3-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]benzoate

HRID 2215976노트

반응식

HRID 2215976 반응식
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]([C:10]1[S:11][C:12]([S:25][CH3:26])=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[CH:28]([O:31][C:32](=[O:49])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[C:34]=1[CH3:48])([CH3:30])[CH3:29].C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:28]([O:31][C:32]([C:33]1[C:34]([CH3:48])=[C:35]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([S:15]([C:13]3[CH:14]=[C:10]([C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:27])=[NH:9])[S:11][C:12]=3[S:25][CH3:26])(=[O:17])=[O:16])[CH:19]=2)[CH:36]=[CH:37][CH:38]=1)=[O:49])([CH3:30])[CH3:29]

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 695866112-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid isopropyl esterHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate2회

생성물 1

HCID 145857657propan-2-yl 2-methyl-3-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]benzoate수율 49.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

The procedure used in Example 1: step c was followed using {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (Example 27 (50 mg, 0.1 mmol)), 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid isopropyl ester ((Example 3: step b) 92 mg, 0.3 mmol), Na2CO3 (2M, 0.4 mL, 0.8 mmol), Pd(PPh3)4 (29.4 mg, 0.025 mmol), ethanol (0.4 mL) and toluene (0.8 mL). Analogous aqueous workup and purification of the crude material by preparative TLC (25% EtOAc in hexanes) yielded the title compound (29 mg, 49%) as a colorless glass. 1H-NMR (CDCl3): δ 7.98 (dt, 1H, J=1.6, 7.6 Hz), 7.93 (m, 2H), 7.79 (t, 1H, J=1.7 Hz), 7.58 (t, 1H, J=7.6 Hz), 7.53 (dt, 1H, J=1.6, 7.6 Hz), 7.36 (s, 1H), 7.30 (d, 1H, J=4.5 Hz), 5.27 (heptet, 1H, J=6.2 Hz), 2.58 (s, 3H), 2.35 (s, 3H), 1.51 (s, 9H), 1.39 (d, 1H, J=6.2 Hz). ESI-MS (m/z): Calcd. for C28H32N2O6S3: 588.8; found: 588.9.

후처리

  1. customAnalogous aqueous workup and purification of the crude material by preparative TLC (25% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-bf492cff01ab4ef6a1d0169c695890e9
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109354B2

반응 노트

불러오는 중…