N-Methoxy-N-methyl-2-phenylacetamide → HCID 66665381, 화합물

HRID 872298노트

반응식

HRID 872298 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:14][CH:12]([CH2:13]2)[O:11][C:10](=[O:15])[NH:9]3)=[CH:4][CH:3]=1.[Li]CCCC.CON(C)[C:24](=[O:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CCCCCC>[C:26]1([CH2:25][C:24]([C:2]2[CH:7]=[CH:6][C:5]([C:8]34[CH2:14][CH:12]([CH2:13]3)[O:11][C:10](=[O:15])[NH:9]4)=[CH:4][CH:3]=2)=[O:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 10419762N-Methoxy-N-methyl-2-phenylacetamideHCID 58229900HCID 58229900, 화합물HCID 178418339Butyllithium2회

생성물 1

HCID 66665381HCID 66665381, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매2회

실험 절차

A solution of 5-(4-bromo-phenyl)-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one (prepared according to WO2009/148916, 4 g) in dry THF (60 mL) was cooled to −78° C. and treated with n-BuLi (6.56 mL of a 2.5M solution in hexane) and stirred for 30 minutes at this temperature before addition of further n-BuLi (13.1 mL of a 2.5M solution in hexane). Stirring was continued at this temperature for 30 minutes before a solution of N-methoxy-N-methyl-benzeneacetamide (prepared according to US6407119B1, 4.6 g) in THF (10 mL) was added. After 10 minutes the reaction was quenched with saturated aqueous ammonium chloride solution, extracted with EtOAc and the combined organic phases washed with brine, filtered and concentrated. The residue was triturated with hexane/EtOAc to give the title compound which was used in the next step without further purification.

후처리

  1. additionwas added
  2. customAfter 10 minutes the reaction was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with EtOAc
  4. washthe combined organic phases washed with brine
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with hexane/EtOAc

출처 및 근거

ORD 기록
ord-390350192f2947f3b4acc0ccb2377f88
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975265B2

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