Tetrabutylammonium Hydroxide → (2S)-3-(3,4-Dihydroxyphenyl)-2-[(tert-butoxycarbonyl)amino]propanoic Acid, Tetrabutylammonium Salt

HRID 229495

반응식

HRID 229495 반응식
[C:1]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:21]=[C:19]([OH:20])[C:17]([OH:18])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[CH2:23]([N+:27]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>CO>[CH2:36]([N+:27]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:37][CH2:38][CH3:39].[OH:20][C:19]1[CH:21]=[C:14]([CH2:13][C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:10]([O-:12])=[O:11])[CH:15]=[CH:16][C:17]=1[OH:18]

참가 물질

4

반응물 2

HCID 2723671Tetrabutylammonium HydroxideHCID 14217229N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine

생성물 1

HCID 46899461(2S)-3-(3,4-Dihydroxyphenyl)-2-[(tert-butoxycarbonyl)amino]propanoic Acid, Tetrabutylammonium Salt수율 83%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
4 °C

실험 절차

A solution of N-Boc-(L)-Dopa (175 g, 0.59 mol) in methanol (1 L) was cautiously mixed with a methanolic solution of tetrabutylammonium hydroxide (1.0 M, 0.55 L) at 0° C. for 30 min. The mixture was then concentrated under reduced pressure and dried by azeotroping with toluene twice. The residue was crystallized after cooling at 4° C. for 16 h. The resulting crystalline solid washed with acetone (400 mL×3), collected on a Buchner funnel, and then dried under high vacuum to afford 245 g (83% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 0.94 (t, J=7.6 Hz, 12H), 1.30 (m, 17H), 1.60 (m, 8H), 3.18 (m, 8H), 4.58 (m, 1H), 5.68 (d, J=5.6 Hz, 1H), 6.30 (d, J=7.6 Hz, 1H), 6.46 (d, J=8.0 Hz, 1H), 6.51 (s, 1H), 8.85 (s, 1H); 8.94 (s, 1H).

후처리

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customdried
  3. customby azeotroping with toluene twice
  4. customThe residue was crystallized
  5. washThe resulting crystalline solid washed with acetone (400 mL×3)
  6. customcollected on a Buchner funnel
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-2add25ad750b4837a590902a199710ae
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563821B2

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