Diisopropylethylamine → HCID 123681539、化合物

HRID 595791

反応式

HRID 595791 の反応式
[B:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([F:13])[CH:5]=1)([OH:3])[OH:2].[CH3:14][S:15]([C:18]1[CH:19]=[C:20]([CH2:24][NH2:25])[CH:21]=[CH:22][CH:23]=1)(=[O:17])=[O:16].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[F:13][C:6]1[CH:5]=[C:4]([B:1]([OH:2])[OH:3])[CH:12]=[CH:11][C:7]=1[C:8](=[O:10])[NH:25][CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([S:15]([CH3:14])(=[O:17])=[O:16])[CH:19]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2760937(3-(Methylsulfonyl)phenyl)methanamineHCID 27632014-Carboxy-3-fluorophenylboronic acid

生成物 1

HCID 123681539HCID 123681539、化合物収率 88.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-borono-2-fluorobenzoic acid (218 mg, 1.2 mmol), (3-(methylsulfonyl)phenyl)-methanamine (200 mg, 1.08 mmol), DIEA (0.754 mL, 4.32 mmol) and TBTU (381 mg, 1.2 mmol) in DMF (2 mL) was stirred at room temperature for 2 days, then the reaction mixture was diluted with water (10 mL), and product precipitated out as gum, and the supernatant was separated via centrifugation, and the gummy residue was sonicated with water (3 mL), and the gummy residue was further dried under high vacuum yielding 3-fluoro-4-(3-(methylsulfonyl)benzylcarbamoyl)-phenylboronic acid (335 mg, 88%) as white foam. LCMS (m/z): 352.1 (MH+), 0.51 min.

後処理

  1. customprecipitated out as gum
  2. customthe supernatant was separated via centrifugation
  3. customthe gummy residue was sonicated with water (3 mL)
  4. customthe gummy residue was further dried under high vacuum

出典と根拠

ORDレコード
ord-3417773766be496d8412b0b4494e335c
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

関連ノート

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