Calcium Carbonate → 2-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester

HRID 239102ノート

反応式

HRID 239102 の反応式
C(=O)([O-])[O-].[Ca+2].Cl[C:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2[N:29]=[C:30]([NH2:32])[S:31][C:25]=2[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2[N:29]=[C:30]([NH:32][C:7]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:8])[S:31][C:25]=2[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

参加物

5

反応物 3

HCID 10112Calcium CarbonateHCID 15891Phenyl chloroformateHCID 11357283tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate

生成物 1

HCID 866860322-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester収率 81.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

39 g calcium carbonate and 36.8 g phenyl chloroformate in 250 mL THF was added to a stirred solution of 50 g 2-amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester in 1 L THF. The reaction mixture was allowed to stir for 15 h at RT. The reaction mixture was filtered through silica gel and the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate and the organic layer was dried over magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was washed with 20% ethyl acetate in hexane to give 60 g of the desired product.

後処理

  1. filtrationThe reaction mixture was filtered through silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. washThe residue was washed with 20% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-1a701deefd8e4b64a92103bf431b87ed
出典データセット
uspto-grants-2014_02
特許番号
US08642774B2

反応ノート

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