Hydrochloric Acid → HCID 86682283, 화합물

HRID 529719

반응식

HRID 529719 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([Cl:10])[CH:3]=1.CON(C)[C:14](=[O:28])[C@@H:15]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:16].C(=O)=O.CC(C)=O.N#N.Cl>C1COCC1.[Cl-].[Na+].O>[Cl:10][C:4]1[CH:3]=[C:2]([C:14](=[O:28])[C@@H:15]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:16])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 30165374-Bromo-2-chloroanisoleHCID 10515879HCID 10515879, 화합물HCID 18522661Acetone cardice

생성물 1

HCID 86682283HCID 86682283, 화합물수율 17.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 4-bromo-2-chloroanisole (3 g, 13.55 mmol) and (S)-benzyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (3.79 g, 14.22 mmol) in THF (33.9 mL) was cooled to −20° C. with dry ice/acetone. To this solution was added isopropylmagnesium chloride lithium chloride complex (22.9 mL, 29.8 mmol) at −20° C. dropwise under N2. After addition, the reaction mixture was warmed up to rt and stirred overnight. The reaction mixture was cooled to −40° C. and slowly poured into a stirred mixture of crushed ice and 30 mL of 1N HCl. The resulting mixture was diluted with 30 mL of brine, extracted with EtOAc (3×50 mL). The organic layer was dried with Na2SO4 and concentrated. The residue was purified by silica gel chromatography, eluted with 0-100% EtOAc in hexane to give (S)-benzyl (1-(3-chloro-4-methoxyphenyl)-1-oxopropan-2-yl)carbamate (0.82 g) as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.05 (s, 1H), 7.92 (d, 1H), 6.98 (d, 1H), 5.93 (d, 1H), 5.29 (m, 1H), 5.16 (s, 2H), 3.99 (s, 3H), 1.43 (d, 3H).

후처리

  1. additionAfter addition
  2. temperatureThe reaction mixture was cooled to −40° C.
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluted with 0-100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-bbb6e3299d8b42cdadc0382a78259e39
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346825B2

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