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Water → (S)-1-[2-hydroxy-4-(4-{hydroxy-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzylsulfanyl)-3-propyl-phenyl]-ethanone

HRID 1818472
ノート
印刷プレビュー

反応式

HRID 1818472 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C@H:22]([OH:31])[C:23]3[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=3)[C:26]#[N:27])=[CH:18][CH:17]=2)=[C:10]([CH2:32][CH2:33][CH3:34])[C:9]=1[OH:35])(=[O:7])[CH3:6].O>CN1CCCC1=O.[Br-].[Zn+2].[Br-]>[OH:35][C:9]1[C:10]([CH2:32][CH2:33][CH3:34])=[C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C@H:22]([OH:31])[C:23]3[CH:30]=[CH:29][CH:28]=[C:25]([C:26]4[NH:27][N:3]=[N:2][N:1]=4)[CH:24]=3)=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:8]=1[C:5](=[O:7])[CH3:6]
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

6

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 66699627(S)-3-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-phenyl]-hydroxy-methyl}-benzonitrile

生成物 1

HCID 178439801(S)-1-[2-hydroxy-4-(4-{hydroxy-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzylsulfanyl)-3-propyl-phenyl]-ethanone収率 31.2%

試薬・触媒・溶媒 2

HCID 10421208
Zinc bromide
触媒
HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

Add sodium azide (66 mg, 0.25 mmol) and zinc bromide (131 mg, 0.50 mmol) to a solution of (S)-3-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-phenyl]-hydroxy-methyl}-benzonitrile (110 mg, 0.25 mmol) in N-methylpyrrolidinone (2.0 ml). Heat the mixture at 140° C. for 12 hours, then cool to room temperature and stir for 18 hours. Pour the mixture into water (25 ml) and stir the solid suspension for 20 minutes. Filter and wash the filtered solid with water. Dissolve the solid in a 1N HCl (25 ml) and ethyl acetate (20 ml) mixture. Extract the aqueous layer with ethyl acetate (25 ml), combine the organic extracts, then wash with water, brine, dry over sodium sulfate and concentrate. Purify the crude product via reverse phase HPLC using a gradient of 90:10 to 20:80 (water/0.1% TFA):acetonitrile as eluent to give the title compound (37 mg, 31%). MS (m/z) 473 (M−H). 1H NMR (400 MHz, DMSO-d6) 12.83 (s, 1H), 8.13-8.11 (m, 1H), 7.89-7.86 (m, 1H), 7.72 (d, 1H), 7.59-7.51 (m, 2H), 7.41-7.37 (m, 4H), 6.96 (d, 1H), 5.60 (s, 1H), 4.30 (s, 2H), 2.65-2.60 (m, 5H), 1.45 (sextet, 2H), 0.90 (t, 3H).

後処理

  1. temperaturecool to room temperature
  2. stirringstir the solid suspension for 20 minutes
  3. filtrationFilter
  4. washwash the filtered solid with water
  5. dissolutionDissolve the solid in a 1N HCl (25 ml) and ethyl acetate (20 ml) mixture
  6. extractionExtract the aqueous layer with ethyl acetate (25 ml)
  7. washwash with water, brine
  8. dry with materialdry over sodium sulfate
  9. concentrationconcentrate
  10. customPurify the crude product via reverse phase HPLC

出典と根拠

ORDレコード
ord-81803f23fac94ed7a6f0efa235e42263
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07598423B2

反応ノート

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