Ethanol → tert-butyl 2-[[3-methyl-2-[5-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonyl-3-pyridinyl]phenyl]methoxy]acetate

HRID 723092ノート

反応式

HRID 723092 の反応式
[C:1]([O:5][C:6](=[O:26])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1B1OC(C)(C)C(C)(C)O1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O:31][C:32](=[O:53])[NH:33][C:34]([C:36]1[S:37][C:38]([S:51][CH3:52])=[C:39]([S:41]([C:44]2[CH:45]=[N:46][CH:47]=[C:48](Br)[CH:49]=2)(=[O:43])=[O:42])[CH:40]=1)=[NH:35])([CH3:30])([CH3:29])[CH3:28].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.CCOC(C)=O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[C:48]1[CH:47]=[N:46][CH:45]=[C:44]([S:41]([C:39]2[CH:40]=[C:36]([C:34]([NH:33][C:32]([O:31][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:53])=[NH:35])[S:37][C:38]=2[S:51][CH3:52])(=[O:43])=[O:42])[CH:49]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 69586495[3-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-acetic acid tert-butyl esterHCID 145857652tert-butyl N-[4-[(5-bromo-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

生成物 1

HCID 145857618tert-butyl 2-[[3-methyl-2-[5-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonyl-3-pyridinyl]phenyl]methoxy]acetate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

The procedure as in Example 1: step c was followed using [3-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-acetic acid tert-butyl ester (252.2 mg, 0.62 mmol, Example 131: step d), {[4-(5-Bromo-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (75.9 mg, 0.15 mmol, Example 128: step a), Pd(PPh3)4 (35 mg, 0.03 mmol), aqueous Na2CO3 (2M, 1 mL), ethanol (1 mL) and toluene (2 mL). The reaction was heated to 80° C. for 24 hours. The reaction mixture was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and removal of the solvents in vacuo was followed by purification by flash column chromatography (SiO2) (30% EtOAc in hexanes) of the residue yielded the title compound (460 mg) as a brown oil. ESI-MS (m/z): Calcd. for C30H37N3O7S3: 648.2 (M+1) found: 647.9.

後処理

  1. washwashed with brine
  2. customThe organic layers were dried
  3. custom(MgSO4) and removal of the solvents in vacuo
  4. customwas followed by purification by flash column chromatography (SiO2) (30% EtOAc in hexanes) of the residue

出典と根拠

ORDレコード
ord-2df6961ccc8b4b51984e60ed57441395
出典データセット
uspto-grants-2006_11
特許番号
US07138530B2

反応ノート

読み込み中…