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Hydrochloric Acid → 6-((1S,3R)-1-biphenyl-4-ylmethyl-3-carboxy-butylcarbamoyl)-4-oxo-4H-pyran-2-carboxylic acid

HRID 2384023
ノート
印刷プレビュー

反応式

HRID 2384023 の反応式
C([O:8][C:9]([C@H:11]([CH3:40])[CH2:12][C@H:13]([NH:27][C:28]([C:30]1[O:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][C:32](=[O:39])[CH:31]=1)=[O:29])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)=[O:10])C1C=CC=CC=1.B(Cl)(Cl)Cl.Cl>C(Cl)Cl>[C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:19]=[CH:20][C:15]([CH2:14][C@@H:13]([NH:27][C:28]([C:30]2[O:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][C:32](=[O:39])[CH:31]=2)=[O:29])[CH2:12][C@H:11]([C:9]([OH:10])=[O:8])[CH3:40])=[CH:16][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 25135Boron TrichlorideHCID 866482066-((1S,3R)-3-benzyloxycarbonyl-1-biphenyl-4-ylmethyl-butylcarbamoyl)-4-oxo-4H-pyran-2-carboxylic acid

生成物 1

HCID 596081716-((1S,3R)-1-biphenyl-4-ylmethyl-3-carboxy-butylcarbamoyl)-4-oxo-4H-pyran-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Next, to a solution of 6-((1S,3R)-3-benzyloxycarbonyl-1-biphenyl-4-ylmethyl-butylcarbamoyl)-4-oxo-4H-pyran-2-carboxylic acid (100 mg, 0.185 mmol) in methylene chloride (5 mL) is added BCl3 (65.1 mg, 0.556 mmol) and the mixture is stirred at room temperature for 10 minutes. The mixture is acidified to pH 2-3 with aqueous 1M HCl and is extracted with ethyl acetate. The organic phase is washed with water and brine and is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by preparative HPLC using a gradient of 10-100% MeCN/water (0.1% TFA) to elute the product. The proper fractions are lyophilized to furnish 6-((1S,3R)-1-biphenyl-4-ylmethyl-3-carboxy-butylcarbamoyl)-4-oxo-4H-pyran-2-carboxylic acid. MS 450.1 (M+1); 1H-NMR (400 Hz, DMSO-d6); δ ppm 1.07 (d, J=7.07 Hz, 3H), 1.59 (m, 1H), 1.88 (m, 1H), 2.45 (m, 1H), 2.84 (d, J=6.69 Hz, 2H), 4.19 (m, 1H), 6.84 (s, 1H), 6.93 (s, 1H), 7.32 (dd, J=8.08 Hz, 6.57 Hz, 3H), 7.45 (t, J=7.83 Hz, 2H), 7.58 (d, J=8.21 Hz, 2H), 7.64 (d, J=7.33 Hz, 2H), 8.61 (d, J=8.72 Hz, 1H).

後処理

  1. extractionis extracted with ethyl acetate
  2. washThe organic phase is washed with water and brine
  3. dry with materialis dried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by preparative HPLC
  6. washto elute the product

出典と根拠

ORDレコード
ord-6407f1d5e26244a4be1d42a5862cd292
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263629B2

反応ノート

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