Water → 5-(3-acetylamino-phenyl)-2-methyl-thiazole-4-carboxylic Acid Methyl Ester

HRID 560260ノート

反応式

HRID 560260 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:17])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[O:4].[CH3:18][CH2:19][O:20]C(C)=O.O>CN(C1C=CN=CC=1)C.C(OC(=O)C)(=O)C.CCOCC>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:17])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:19](=[O:20])[CH3:18])[CH:11]=1)=[O:4]

参加物

7

反応物 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 66844939HCID 66844939、化合物

生成物 1

HCID 668444965-(3-acetylamino-phenyl)-2-methyl-thiazole-4-carboxylic Acid Methyl Ester

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 3283Diethyl Ether溶媒HCID 7918Acetic Anhydride溶媒

実験手順

TEA (14.2 mmol) and DMAP (4.05 mmol) are added successively to a solution of 5-(3-amino-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl ester (4.05 mmol) in acetic anhydride (25 mL). After stirring for 30 min EtOAc and water are added, the layers are separated and the aq. layer is extracted once with EtOAc. The combined organic layers are washed with sat. aq. NH4Cl solution, sat. aq. NaHCO3 solution and water, dried over MgSO4 and concentrated in vacuo to give a crude product which is diluted with ether. The obtained suspension is filtered. The residue is washed with ether and dried in vacuo to give the desired product which is used without further purification. LC-MS: tR=0.81 min; [M+H]+=291.3.

後処理

  1. additionare added
  2. customthe layers are separated
  3. extractionthe aq. layer is extracted once with EtOAc
  4. washThe combined organic layers are washed with sat. aq. NH4Cl solution, sat. aq. NaHCO3 solution and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. filtrationThe obtained suspension is filtered
  9. washThe residue is washed with ether
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-4c966a98e9a747b0a9746e47849302f0
出典データセット
uspto-grants-2011_11
特許番号
US08063099B2

反応ノート

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