Benzoyl Peroxide → Glycine, N-methyl-, ethyl ester

HRID 636545노트

반응식

HRID 636545 반응식
[OH:1][C:2]1[C:18]([OH:19])=[CH:17][CH:16]=[C:15]2[C:3]=1[CH2:4][C:5]1[C:6]3[CH:7]2[CH2:8][NH:9][CH2:10][C:11]=3[CH:12]=[CH:13][CH:14]=1.C1NCC2=CC=CC3=C2[C@@H]1C1C=C[C:34]([OH:37])=[C:33](O)C=1C3.C[N:40]1[CH2:49][C:48](=[O:50])C2C(=CC=CC=2)[CH2:41]1.C(OC(C1C(C)=CC=CC=1)=O)C.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[CH2:8]1[NH:9][CH2:10][C:11]2=[CH:12][CH:13]=[CH:14][C:5]3=[C:6]2[C@@H:7]1[C:15]1[CH:16]=[CH:17][C:18]([OH:19])=[C:2]([OH:1])[C:3]=1[CH2:4]3.[CH2:34]([O:37][C:48](=[O:50])[CH2:49][NH:40][CH3:41])[CH3:33]

참가 물질

8

반응물 6

HCID 7187Benzoyl PeroxideHCID 66598Ethyl 2-methylbenzoateHCID 67184N-bromobutanimideHCID 52494902,3,7,11b-Tetrahydro-1H-dibenzo[de,h]isoquinoline-8,9-diolHCID 9816455DinapsolineHCID 106308122-Methyl-2,3-dihydroisoquinolin-4(1H)-one

생성물 2

HCID 95849Glycine, N-methyl-, ethyl esterHCID 9816455Dinapsoline

실험 절차

One compound provided in accordance with the present invention is (±)-8,9-dihydroxy-2,3,7,11b-tetrahydro-1H-naphtho[1,2,3-de] isoquinoline denominated hereinafter as “dinapsoline.” Dinapsoline is synthesized from 2-methyl-2,3-dihydro-4(1H)-isoquinolone according to the procedure depicted generally in FIGS. 1 and 2. Side chain bromination of ethyl-o-toluate (5a) with NBS in the presence of benzoyl peroxide produced compound 5b. Alkylation of sarcosine ethyl ester with compound 5b afforded compound 6, which after Dieckmann condensation and subsequent decarboxylation on acidic hydrolysis yielded compound 7.

후처리

  1. customOne compound provided in accordance with the present invention

출처 및 근거

ORD 기록
ord-20c0db3282de49a1a45ad3080f2e2a79
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194423B1

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