Triethylamine → 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one

HRID 639049

反応式

HRID 639049 の反応式
[O:1]=[C:2]1[CH2:7][S:6][C:5]2[CH:8]=[CH:9][C:10]([C:12](O)=[O:13])=[N:11][C:4]=2[NH:3]1.C(N(CC)CC)C.ClC(OCC(C)C)=O>C1COCC1>[OH:13][CH2:12][C:10]1[CH:9]=[CH:8][C:5]2[S:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=2[N:11]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 218737873-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid

生成物 1

HCID 116080936-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one収率 74.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (500 mg) in THF (24 mL) with triethylamine (0.396 mL) was cooled to −10° C. and isobutyl chloroformate (0.339 ml) added. After 20 minutes the suspension was filtered through kieselguhr into an ice-cooled solution of sodium borohydride (272 mg) in water (8 mL), the mixture stirred 30 minutes and the pH reduced to 7 with dilute HCl. The solvent was evaporated and the residue triturated under water. The product was filtered and dried under vacuum to give a white solid (346 mg); MS (APCl−) m/z 195 ([M−H]−, 50%), 165(100%).

後処理

  1. filtrationAfter 20 minutes the suspension was filtered through kieselguhr into an ice-
  2. temperaturecooled solution of sodium borohydride (272 mg) in water (8 mL)
  3. customThe solvent was evaporated
  4. customthe residue triturated under water
  5. filtrationThe product was filtered
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-2c0a4184e7ae4663ae54c2acb62497bb
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

関連ノート

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