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

HRID 560260노트

반응식

HRID 560260 반응식
[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]

참가 물질

7

반응물 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 66844939HCID 66844939, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매HCID 7918Acetic Anhydride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4c966a98e9a747b0a9746e47849302f0
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063099B2

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