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

HRID 639049

반응식

HRID 639049 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-2c0a4184e7ae4663ae54c2acb62497bb
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691850B2

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