Diisopropylethylamine → 1,1-Dimethylethyl (2-{[(5-bromo-3-thienyl)carbonyl]amino}-2-phenylethyl)carbamate

HRID 1967098노트

반응식

HRID 1967098 반응식
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.[NH2:10][CH:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([NH:10][CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:9])[CH:3]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 2771847tert-butyl N-(2-amino-2-phenylethyl)carbamateHCID 120399785-Bromothiophene-3-carboxylic acid

생성물 1

HCID 683976791,1-Dimethylethyl (2-{[(5-bromo-3-thienyl)carbonyl]amino}-2-phenylethyl)carbamate수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-bromo-3-thiophenecarboxylic acid (1 g, 4.85 mmol)[prepared according to J. Org. Chem. 1976, 41, 2350.], 1,1-dimethylethyl (2-amino-2-phenylethyl)carbamate (1.1 g, 4.85 mmol)[from Preparation 1] and diisopropylethyl amine (2.5 mL, 14.60 mmol) in DCM (50 mL) at 25° C. was added PyBrOP (2.5 g, 5.30 mmol) in one portion. After 16 h, the solution was partitioned between H2O and washed with DCM. The combined organic fractions were dried (Na2SO4), concentrated and purified via column chromatography (silica, 1% MeOH in DCM) affording the title compound (1.4 g, 68%) as a white solid: LC-MS (ES) m/z=426 (M+H)+.

후처리

  1. customthe solution was partitioned between H2O
  2. washwashed with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica, 1% MeOH in DCM)

출처 및 근거

ORD 기록
ord-88eee836458641a0b74cb953cc7acd2a
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420690B2

반응 노트

불러오는 중…