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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0

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Water → 3-(5-Chloro-2-ethoxycarbonylmethoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

HRID 237306

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HRID 237306 반응식

[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[OH:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[C:27]([O:30][CH2:31][CH2:32]Br)(=[O:29])[CH3:28].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:28][C:27]([O:30][CH2:31][CH3:32])=[O:29])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질 실험 절차 후처리 출처 및 근거 반응 노트

참가 물질

6

반응물 4

HCID 10796Cesium carbonate

HCID 135641-Acetoxy-2-bromoethane

HCID 673429093-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 673467163-(5-Chloro-2-ethoxycarbonylmethoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester수율 101.1%

시약·촉매·용매 1

HCID 6228

Dimethylformamide

용매

실험 절차

To 3-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (1.5 g, 5.0 mmol) in DMF (20 mL) was added Cs2CO3 (2.1 g, 6.4 mmol), KI (0.84 g, 5.0 mmol) and bromoethyl acetate (0.84 g, 0.55 mL, 5.0 mmol). After 18 h, H2O was added and the mixture extracted with EtOAc (2×). The combined organics were washed with brine and dried. Silica gel chromatography (5-30% EtOAc in hexanes) gave 1.95 g (99%) of the title compound as a clear oil. 1H NMR (CDCl3): 6.91 (dd, J=8.7, 2.4 Hz, 1H), 6.79 (d, J=8.7 Hz, 1H), 6.58 (d, J=2.4 Hz, 1H), 4.91-4.87 (m, 1H), 4.65 (s, 2H), 4.32-4.25 (m, 4H), 4.01 (dd, J=10.5, 4.2 Hz, 2H), 1.44 (s, 9H), 1.30 (t, J=7.1 Hz, 3H).

후처리

extractionthe mixture extracted with EtOAc (2×)
washThe combined organics were washed with brine
customdried

출처 및 근거

ORD 기록: ord-0332a41b701a46da87e8235edf3d21bc
출처 데이터셋: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08642583B2

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