1-Adamantaneacetyl chloride → N-[1-(hydroxymethyl)-2-phenylethyl]-alpha-methyl-alpha-[[tricyclo[3.3.1.13,7]dec-1-ylacetyl)-amino]-1H-indole-3-propanamide

HRID 54843노트

반응식

HRID 54843 반응식
[CH3:1][C@:2]([C:14]([NH:16][C@H:17]([CH2:25][OH:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[NH2:3].[C:27]12([CH2:37][C:38](Cl)=[O:39])[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2>C1COCC1>[OH:26][CH2:25][CH:17]([NH:16][C:14](=[O:15])[C:2]([CH3:1])([NH:3][C:38](=[O:39])[CH2:37][C:27]12[CH2:36][CH:31]3[CH2:30][CH:29]([CH2:35][CH:33]([CH2:32]3)[CH2:34]1)[CH2:28]2)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

4

반응물 2

HCID 27718821-Adamantaneacetyl chlorideHCID 54471265alpha-methyl-D-tryptophyl-L-phenylalaninol

생성물 1

HCID 53928863N-[1-(hydroxymethyl)-2-phenylethyl]-alpha-methyl-alpha-[[tricyclo[3.3.1.13,7]dec-1-ylacetyl)-amino]-1H-indole-3-propanamide수율 113%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of α-methyl-D-tryptophyl-L-phenylalaninol (1 g, 2.85 mmol) and 4-N,N-dimethylaminopyridine (0.35 g, 2.87 mmol ) in dry THF (50 mL ) at 0° C. was treated dropwise, with stirring, with a solution of 1-adamantylacetyl chloride (0.605 g, 2.85 mmol). A precipitate formed immediately. The reaction mixture was left until all starting materials were consumed as assayed by TLC and IR spectroscopy. The final TLC showed three spots (10% MeOH:90% CH2Cl2). The reaction mixture was washed with 1M citric acid solution and extracted into ethyl acetate. The organic phase was then washed with water and dried over MgSO4. Concentration in vacuo gave a syrup (1.7 g) which was chromatographed over silica using 2% MeOH:98% CH2Cl2 as eluant to yield the title compound (1.35 g, 90%) as a white solid crystallized from ethyl acetate-hexane, mp 91°-94° C. (EtOAc-hexane); IR (KBr) 3304 and 1652 cm-1 ; NMR (CDCl3) δ1.48 (9H, m), 1.59 (6H, m), 1.76 (2H, q, J 13 Hz), 1.9 (3H, m), 2.74 (2H, d, J 7Hz), 3.21 (1H, half ABq J 14.5Hz), 3.30 (1H, 6, J 6Hz), 3.40 (1H, half Abq J 14.5Hz), 3.45 (1H, m), 3.70 (1H, m), 4.16 (1H, m), 5.91 (1H, s), 6.38 (1H, d, J 8Hz), 6.92 (1H, d, J 3Hz), 7.07-7.27 (7 H, m), 7.35 (1H, d, J 8Hz), 7.56 (1H, d, J 8Hz) and 8.54 (1H, s); Anal. (C33H41N3O3.0.25 H2O), C, H, N.

후처리

  1. customA precipitate formed immediately
  2. waitThe reaction mixture was left until all starting materials
  3. customwere consumed
  4. washThe reaction mixture was washed with 1M citric acid solution
  5. extractionextracted into ethyl acetate
  6. washThe organic phase was then washed with water
  7. dry with materialdried over MgSO4
  8. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-2078aab5f25749d49d1c4d353863d7f2
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622983

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