1,2-Dichloroethane → N-isobutyl-2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanamide

HRID 1175588ノート

反応式

HRID 1175588 の反応式
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)=[CH:9][CH:8]=1)([CH3:6])[C:3](O)=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:36][CH:37]([CH3:40])[CH2:38][NH2:39]>C(Cl)Cl>[CH2:38]([NH:39][C:3](=[O:4])[C:2]([CH3:6])([C:7]1[CH:8]=[CH:9][C:10]([B:13]2[O:14][C:15]([CH3:20])([CH3:21])[C:16]([CH3:18])([CH3:19])[O:17]2)=[CH:11][CH:12]=1)[CH3:1])[CH:37]([CH3:40])[CH3:36]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 6558IsobutylamineHCID 757711-HydroxybenzotriazoleHCID 684558452-Methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid

生成物 1

HCID 68776318N-isobutyl-2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanamide収率 99.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid (example 20d) (10 g, 34.46 mmol), EDC (7.26 g, 37.91 mmol) and HOBt (5.12 g, 37.91 mmol) were mixed in DCM (350 mL) and stirred for 5 minutes then 2-methylpropan-1-amine (3.6 mL, 36.19 mmol) was added. The reaction mixture was stirred at room temperature overnight then diluted with dichloromethane and washed successively with aq. HCl (0.5N), water, aq. NaHCO3, water and brine, dried over MgSO4, filtered and evaporated. The residue was crystallized from EtOAc/hexane to give 11.8 g of product as a white solid in 99% yield. 1H NMR (400 MHz, CDCl3): δ 0.76-0.78 (d, 6H), 1.35(s, 12H), 1.57 (s, 6H), 1.62 (m, 1H), 2.97 (t, 2H), 5.15 (br-s, 1H), 7.38-7.40 (d, 2H), 7.79-7.81 (d, 2H). MS (M+H, 346).

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washwashed successively with aq. HCl (0.5N), water, aq. NaHCO3, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from EtOAc/hexane

出典と根拠

ORDレコード
ord-63dd0270036349a2a6a70a70cb146085
出典データセット
uspto-grants-2010_11
特許番号
US07842324B2

反応ノート

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