Hydrochloric Acid → Methanesulfonic acid 2-[3-benzyloxy-5-fluoro-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-5-methylphenyl ester

HRID 889249ノート

反応式

HRID 889249 の反応式
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([OH:17])[C:3]=1[N:18]1[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH2:19]1.Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:29]=1[O:35][S:36]([CH3:39])(=[O:38])=[O:37].C([O-])([O-])=O.[Na+].[Na+].Cl>COCCOC.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>[CH2:27]([O:17][C:4]1[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[C:3]=1[N:18]1[CH2:19][C:20](=[O:25])[NH:21][S:22]1(=[O:23])=[O:24])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:29]=1[O:35][S:36]([CH3:39])(=[O:38])=[O:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 684295315-[2-Fluoro-6-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-oneHCID 86638983Methanesulfonic acid 2-bromomethyl-5-methylphenyl ester

生成物 1

HCID 86638984Methanesulfonic acid 2-[3-benzyloxy-5-fluoro-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-5-methylphenyl ester

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-[2-fluoro-6-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (150 mg, 0.325 mmol) and Pd(PPh3)4 (38 mg, 0.0325 mmol) in DME (2 mL) is heated at 60° C. under argon for 1 h. Then methanesulfonic acid 2-bromomethyl-5-methylphenyl ester (181 mg, 0.65 mmol) and Na2CO3 (2N solution, 0.81 mL) is added. The mixture is heated at 120° C. in a microwave for 20 min. 1N HCl is added and the reaction mixture is extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4 and filtered. The filtrate is concentrated to give the title compound and it is used directly in the next step: MS (M−H)−=533.

後処理

  1. temperatureThe mixture is heated at 120° C. in a microwave for 20 min
  2. extractionthe reaction mixture is extracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated

出典と根拠

ORDレコード
ord-45a47038d13d456f9e5fd776cedc860e
出典データセット
uspto-grants-2012_08
特許番号
US08252820B2

反応ノート

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