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

HRID 1175588노트

반응식

HRID 1175588 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-63dd0270036349a2a6a70a70cb146085
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842324B2

반응 노트

불러오는 중…