N-Hydroxyphthalimide → Benzyl 5-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]-3-chlorobenzoate

HRID 1698860노트

반응식

HRID 1698860 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:43]1[C:47](=[O:48])[C:46]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:45]2[C:44]1=[O:53].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:53]=[C:44]1[C:45]2[C:46](=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:47](=[O:48])[N:43]1[O:22][CH2:21][CH2:20][CH2:19][O:18][C:16]1[CH:17]=[C:2]([Cl:1])[CH:3]=[C:4]([CH:15]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18322176Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

생성물 1

HCID 18322169Benzyl 5-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]-3-chlorobenzoate수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of alcohol 26 (5.96 g, 18.6 mmol), triphenylphosphine (5.40 g, 20.5 mmol), and N-hydroxyphthalirnide (2.10 g, 20.5 mmol) in tetrahydrofuran (186 mL) was cooled to 0° C. and reacted slowly with diethyl azodicarboxylate (3.50 mL, 22.3 mmol). After warming to ambient temperature and stirring 16 hrs, the reaction was concentrated in vacuo and purified by chromatography on silica gel (10% ethyl acetate in hexanes) giving product 27 (5.18 g, 60%). 1H NMR (300 MHz, CDCl3) δ 7.83 (dd, 2H, J=5.6 Hz, 3.1 Hz), 7.75 (dd, 2H, J=5.6 Hz, 3.1 Hz), 7.63 (t, 1H, J=1.5 Hz), 7.51 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.40 (m, 5H), 7.12 (t, 1H, J=2.3 Hz), 5.35 (s, 2H), 4.41 (t, 2H, J=6.1 Hz), 4.28 (t, 2H, J=6.1 Hz), 2.25 (pentet, 2H, J=6.1 Hz).

후처리

  1. concentrationthe reaction was concentrated in vacuo
  2. custompurified by chromatography on silica gel (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-8250fae45fd7470892bbf7e209111e20
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344466B2

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