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Potassium Sodium Tartrate → (S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-N-(5-fluoropyridin-2-yl)-2-hydroxypropanamide

HRID 1098255
ノート
印刷プレビュー

反応式

HRID 1098255 の反応式
C[Al](C)C.[F:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.[Si:13]([O:20][CH:21]1[CH2:24][N:23]([CH2:25][C@H:26]([OH:31])[C:27](OC)=[O:28])[CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Si:13]([O:20][CH:21]1[CH2:24][N:23]([CH2:25][C@H:26]([OH:31])[C:27]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([F:5])=[CH:11][N:10]=2)=[O:28])[CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 9357Potassium Sodium TartrateHCID 27377012-Amino-5-fluoropyridineHCID 16682925TrimethylaluminumHCID 57504648(S)-methyl 3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-hydroxypropanoate

生成物 1

HCID 57504700(S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-N-(5-fluoropyridin-2-yl)-2-hydroxypropanamide収率 51.7%

試薬・触媒・溶媒

2
HCID 1140Toluene溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Trimethylaluminium (2M solution in toluene) (15.89 mL, 31.79 mmol) was added to 5-fluoropyridin-2-amine (3.10 g, 27.64 mmol) in toluene (80 mL) cooled to 0° C. under nitrogen over a period of 10 minutes. The resulting solution was stirred at 0° C. for 10 minutes. (S)-methyl 3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-hydroxypropanoate (Intermediate AD3) (8 g, 27.64 mmol) in toluene (20 mL) was added over 10 minutes and the reaction was allowed to warm to room temperature and then heated at 90° C. for 2 hours. The reaction mixture was cooled and poured into a 20% solution of Rochelle's salt (50 mL), diluted with ethyl acetate (200 mL) and stirred for 2 hours. The organic phase was separated, washed with water and brine, dried (MgSO4) filtered and evaporated. The crude product was purified by flash silica chromatography, elution gradient 80 to 100% EtOAc in isohexane to afford the product (5.28 g, 51.7%). 1H NMR (400 MHz, CDCl3) δ 0.028 (3H, s), 0.033 (3H, s), 0.87 (9H, s), 2.90 (2H, d), 3.02-3.08 (2H, m), 3.68-3.74 (2H, m), 4.00 (1H, t), 4.41-4.48 (1H, m), 7.41-7.45 (1H, m), 8.15 (1H, d), 8.21-8.24 (1H, m), 9.85 (1H, s); m/z (ES+) (M+H)+=370; HPLC tR=1.97 min.

後処理

  1. temperatureto warm to room temperature
  2. temperatureheated at 90° C. for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. stirringstirred for 2 hours
  5. customThe organic phase was separated
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified by flash silica chromatography, elution gradient 80 to 100% EtOAc in isohexane

出典と根拠

ORDレコード
ord-e52f56d2c5c7458db7eaf4813e9f3194
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08143263B2

反応ノート

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