Diisopropylethylamine → HCID 123681539, 화합물

HRID 595791

반응식

HRID 595791 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 123681539HCID 123681539, 화합물수율 88.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3417773766be496d8412b0b4494e335c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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