Brucine → Brucine

HRID 256487

반응식

HRID 256487 반응식
[Cl:1][C:2]1[CH:6]([OH:7])[C:5]([Cl:9])([Cl:8])[C:4]([OH:13])([C:10]([OH:12])=[O:11])[CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[C:20]2[C@@:22]34[C@H:30]5[N:31]([C:32]([CH2:34][C@@H:35]6[O:36][CH2:37][CH:38]=[C:39]7[CH2:40][N:25]([C@H:26]3[CH2:27][C@@H:28]7[C@H:29]56)[CH2:24][CH2:23]4)=[O:33])[C:19]2=[CH:18][C:17]=1[O:41][CH3:42]>CO>[CH3:14][O:15][C:16]1[CH:21]=[C:20]2[C@@:22]34[C@H:30]5[N:31]([C:32]([CH2:34][C@@H:35]6[O:36][CH2:37][CH:38]=[C:39]7[CH2:40][N:25]([C@H:26]3[CH2:27][C@@H:28]7[C@H:29]56)[CH2:24][CH2:23]4)=[O:33])[C:19]2=[CH:18][C:17]=1[O:41][CH3:42].[Cl:1][C:2]1[C@@H:6]([OH:7])[C:5]([Cl:9])([Cl:8])[C@:4]([OH:13])([C:10]([OH:12])=[O:11])[CH:3]=1

참가 물질

5

반응물 2

HCID 442021BrucineHCID 11288097HCID 11288097, 화합물

생성물 2

HCID 442021BrucineHCID 13216816HCID 13216816, 화합물

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To (±)-3,5,5-trichloro-1,4-dihydroxycyclopent-2-ene-1-carboxylic acid (3) (A. W. Burgstahler, T. B. Lewis, and M. O. Abdel-Rahman, J. Org. Chem., 1966, 31, 3516; C. J. Moye and S. Sternhell, Aust. J. Chem., 1966 19, 2017) (10 g, 40.4 mmol) in methanol (1l) was added (-)-brucine (15.94 g, 40.4 mmol) in methanol (1l). Crystallisation at room temperature gave two crops (8.50 and 2.33 g respectively) of relatively pure (-)-brucine salt of the acid (4), [α]D25 - 110° (c 0.24, CHCl3). Recrystallisation from methanol gave the pure (-)-brucine salt of the acid (4) (9.64 g, 74%) as colourless plates, m.p. 143°-146°, [α]D25 -120° (c 0.247, CHCl3 ) (Found : C, 54.1; H, 4.85; Cl, 16.4; N, 4.05. C29H31Cl3N2O8 requires C, 54.25; H, 4.85; Cl 16.55; N, 4.35%).

후처리

  1. customCrystallisation at room temperature

출처 및 근거

ORD 기록
ord-40c7b89abe6f40758e95c550ea5ecd21
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04703127

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