5,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide → 3-[(1S)-3-hydroxy-1-[(5,5,6,6-tetramethyl-4,4-dioxo-1,4,3-oxathiazin-2-yl)amino]propyl]benzonitrile

HRID 72363노트

반응식

HRID 72363 반응식
[CH3:1][C:2]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][C:5](OC2C=CC([N+]([O-])=O)=CC=2)=[N:4][S:3]1(=[O:21])=[O:20].Cl.[NH2:24][C@H:25]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33])[CH2:26][CH2:27][OH:28]>ClCCl.C(N(CC)C(C)C)(C)C>[OH:28][CH2:27][CH2:26][C@@H:25]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33])[NH:24][C:5]1[O:6][C:7]([CH3:8])([CH3:9])[C:2]([CH3:1])([CH3:22])[S:3](=[O:20])(=[O:21])[N:4]=1

참가 물질

5

반응물 2

HCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxideHCID 867054533-((S)-1-amino-3-hydroxypropyl)benzonitrile hydrochloride

생성물 1

HCID 1784316813-[(1S)-3-hydroxy-1-[(5,5,6,6-tetramethyl-4,4-dioxo-1,4,3-oxathiazin-2-yl)amino]propyl]benzonitrile수율 59.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 81531Diisopropylethylamine용매

실험 절차

100 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 97 mg of 3-((S)-1-amino-3-hydroxypropyl)benzonitrile hydrochloride were dissolved in 5 ml of dichloromethane and 0.25 ml of N,N-diisopropylethylamine, and the mixture was stirred at room temperature for 16 hours. Subsequently, the reaction solution was diluted with 20 ml of dichloromethane, and washed with 10 ml of 10% aqueous ammonia solution and with 10 ml of 1 N aqueous hydrochloric acid. The two aqueous phases were extracted once again with 20 ml of ethyl acetate, and the combined organic phases were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (66 mg) was thus obtained with a molecular weight of 365.5 g/mol (C17H23N3O4S); MS (ESI): m/e=366 (M+H+).

후처리

  1. washwashed with 10 ml of 10% aqueous ammonia solution and with 10 ml of 1 N aqueous hydrochloric acid
  2. extractionThe two aqueous phases were extracted once again with 20 ml of ethyl acetate
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified in a purification laboratory by means of preparative HPLC

출처 및 근거

ORD 기록
ord-908ccb423f614e01ae1d316f1153bec8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828994B2

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