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Triethylamine → (1R,2R)-2-(4-Chlorophenyl)-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-methyloxazole-5-carboxamide

HRID 1419701
ノート
印刷プレビュー

反応式

HRID 1419701 の反応式
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=O)=[CH:4][CH:3]=1.C(Cl)(=O)[C:17](Cl)=[O:18].[NH2:22][C@H:23]([CH3:40])[C@:24]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[F:39])([OH:31])[CH2:25][N:26]1[CH:30]=[N:29][CH:28]=[N:27]1.C(N(CC)CC)C>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:13][C:11]([C:17]([NH:22][C@H:23]([CH3:40])[C@:24]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=3[F:39])([OH:31])[CH2:25][N:26]3[CH:30]=[N:29][CH:28]=[N:27]3)=[O:18])=[C:9]([CH3:10])[N:8]=2)=[CH:14][CH:15]=1
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 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1241470(2S)-2-[(4-chlorophenyl)formamido]propanoic acidHCID 10967497(2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

生成物 1

HCID 5480567(1R,2R)-2-(4-Chlorophenyl)-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-methyloxazole-5-carboxamide

試薬・触媒・溶媒

2
HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A solution of N-(4-chlorobenzoyl)-L-alanine (1.46 g, 6.41 mmol) in benzene (35 mL) was treated with oxalyl chloride (0.55 mL, 6.41 mmol) at 45° C. for 3 h. Next, a solution of (2R,3R)-3-amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1.72 g, 6.41 mmol) and triethylamine (2.2 mL) in CHCl2 (20 mL) was slowly added and the reaction mixture was stirred at 0° C. for 0.5 h. The crude product was then poured into cold water and extracted with CHCl3. The organic solution was dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give a mixture of several products (TLC) from which the title compound was isolated by flash chromatography as a white solid (140 mg): mp 89°-93° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.04 (d, J=8.5, 2H, arom), 7.79 (s, 1H, triazole), 7.78 (s, 1H, triazole), 7.49 (d, J=8.5, 2H, arom), 7.37 (dt, Jd =6.5, Jt =8.8, 1H, arom), 6.8-6.6 (m, 3H, arom, NH), 5.38 (d, J=1.1, 1H, OH), 5.04 (d, J=14.3, 1H, TrCH(H)), 4.96 (br quint, J=7, 1H, CHMe), 4.53 (d, J=14.3, 1H, TrCH(H)), 2.60 (s, 3H, Me-oxazole), 1.04 (d, J=6.8, 3H, MeCH); HPLC-MS 263 and 265 (ethylaminoacyl group, C13H12ClN2O2), 220 and 222 (acyl group, C11H7ClNO2), 224 (Tr--CH2COHAr, C10H8F2N3O); [α]D =-141° (c 0.5, CHCl3). Analysis calculated for C23H20ClF2N5O3 : C 56.62; H 4.13; N 14.35. Found: C 56.41; H 4.19; N 14.50.

後処理

  1. extractionextracted with CHCl3
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto give

出典と根拠

ORDレコード
ord-4b315e11eb6247d8b18657df3d59e545
出典データセット
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05888941

反応ノート

読み込み中…

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