Triethylamine → alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol

HRID 1461857노트

반응식

HRID 1461857 반응식
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH:25]=O)[N:24]=1)(=[O:18])[CH3:17].C(N(CC)CC)C.[BH4-].[Na+]>CO>[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][NH:2][CH2:3][CH:4]([OH:15])[C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=2)[N:24]=1)(=[O:18])[CH3:17]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochlorideHCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamide

생성물 1

HCID 14719582alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol수율 82%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

α-(Aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride (2.88 g) and 2-acetamido-4-formyl-thiazole (2.1 g) were suspended in 14 ml methanol, and 1.8 ml triethylamine was added dropwise to this suspension with stirring. The resulting solution was heated under reflux for 30 minutes, and 0.70 g sodium borohydride was added in small portions with stirring under ice cooling. The crystals which separated out were collected by filtration, washed with water and methanol in that order and vacuum-dried, giving 3.55 g of α-[[[(2-acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol, m.p. 204°-206° C.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 30 minutes
  3. stirringwith stirring under ice cooling
  4. customThe crystals which separated out
  5. filtrationwere collected by filtration
  6. washwashed with water and methanol in that order
  7. customvacuum-dried

출처 및 근거

ORD 기록
ord-387554274ad54f5ab4272816b76e8e1a
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05077406

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