Sodium Carbonate → HCID 68425473、化合物

HRID 1945087ノート

反応式

HRID 1945087 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]([O:16][C:14]([NH:13][C@H:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:21])[CH:27]=2)=[CH:3][CH:4]=1)[C:10]([OH:12])=[O:11])=[O:15])([CH3:20])([CH3:19])[CH3:18]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 7020327(2R)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

生成物 1

HCID 68425473HCID 68425473、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

(R)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid (4.0 g, 11.6 mmol), 3-chlorophenylboronic acid (2.36 g, 15.11 mmol), Pd(PPh3)4 (0.067 g, 0.058 mmol) and 2M Na2CO3 aqueous solution (8.0 mL) are refluxed in 1,2-dimethmethane (70 mL) for 2.5 h under N2 atomosphere. After cooling to room temperature, the reaction mixture is diluted with EtOAc and washed with 1M HCl and brine. The organic layer is dried over Na2SO4 and concentrated. The residue is purified by flash column chromatography (silica gel, DCM/10% MeOH in DCM=100:0 to 0:100) to give (R)-2-tert-butoxycarbonylamino-3-(3′-chloro-biphenyl-4-yl)-propionic acid (containing impurities). HPLC retention time=1.56 minutes (condition A): MS (m+1)=376.

後処理

  1. washwashed with 1M HCl and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash column chromatography (silica gel, DCM/10% MeOH in DCM=100:0 to 0:100)

出典と根拠

ORDレコード
ord-69c841275f9445c5b1d04720c5c16800
出典データセット
uspto-grants-2013_03
特許番号
US08394853B2

反応ノート

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