Potassium bisulfate → alpha-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-(thiazol-5-yl)methylamino-benzyl alcohol

HRID 275875

반응식

HRID 275875 반응식
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=1.[CH:26]1[N:30]=[CH:29][S:28][C:27]=1[CH:31]=O.[BH4-].C([Na])#N.S([O-])(O)(=O)=O.[K+]>CO.C(O)(=O)C>[C:16]([O:15][C:13]([NH:12][CH2:11][C:7]1[CH:6]=[C:5]([CH:4]([OH:20])[C:3]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:2]=2[NH:1][CH2:31][C:27]2[S:28][CH:29]=[N:30][CH:26]=2)[CH:10]=[CH:9][CH:8]=1)=[O:14])([CH3:18])([CH3:19])[CH3:17]

참가 물질

7

반응물 4

HCID 516920Potassium bisulfateHCID 27735771,3-Thiazole-5-carbaldehydeHCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholHCID 178511851HCID 178511851, 화합물

생성물 1

HCID 69696794alpha-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-(thiazol-5-yl)methylamino-benzyl alcohol수율 96.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

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온도
60 °C

실험 절차

In methanol (10 ml) were dissolved 2-amino-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-chlorobenzyl alcohol (1 g) produced in Example (1) and thiazole-5-carboxyaldehyde (0.34 g). To the solution were added acetic acid (0.33 g) and cyano sodium borohydride (0.21 g). The mixture was stirred for one hour at 60° C. The reaction mixture was added to a 5% aqueous solution of potassium hydrogensulfate, followed by extraction with ethyl acetate (50 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give α-(3-tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-(thiazol-5-yl)methylamino-benzyl alcohol (1.22 g) as a colorless amorphous solid product.

후처리

  1. extractionfollowed by extraction with ethyl acetate (50 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by means of a silica gel column chromatography

출처 및 근거

ORD 기록
ord-487c39547e64462aa5b1e8b8cd8ae5f1
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352982B1

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