Diisopropylethylamine → 3-{6-[4-(2-Diisopropylaminoethylamino)benzenesulfonyloxy]benzothiazol-2-yl-carbamoyl}azetidine-1-carboxylic acid tert-butyl ester

HRID 1867977노트

반응식

HRID 1867977 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:48][C:49]1[S:50][C:51]2[CH:57]=[C:56]([O:58][S:59]([C:62]3[CH:67]=[CH:66][C:65]([NH:68][CH2:69][CH2:70][N:71]([CH:75]([CH3:77])[CH3:76])[CH:72]([CH3:74])[CH3:73])=[CH:64][CH:63]=3)(=[O:61])=[O:60])[CH:55]=[CH:54][C:52]=2[N:53]=1>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12](=[O:14])[NH:48][C:49]2[S:50][C:51]3[CH:57]=[C:56]([O:58][S:59]([C:62]4[CH:67]=[CH:66][C:65]([NH:68][CH2:69][CH2:70][N:71]([CH:75]([CH3:77])[CH3:76])[CH:72]([CH3:73])[CH3:74])=[CH:64][CH:63]=4)(=[O:61])=[O:60])[CH:55]=[CH:54][C:52]=3[N:53]=2)[CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 579808584-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl ester

생성물 1

HCID 579808573-{6-[4-(2-Diisopropylaminoethylamino)benzenesulfonyloxy]benzothiazol-2-yl-carbamoyl}azetidine-1-carboxylic acid tert-butyl ester수율 27.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

68 mg of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester, 256 mg of HBTU and 235 μl of DIEA are added to a solution of 4-(2-diisopropylamino-ethylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl ester (inter-mediate 34) (100 mg, 0.225 mmol) in 5 ml of dimethylformamide. The solution obtained is stirred for 20 hours at room temperature. After addition of 50 ml of water, the reaction medium is extracted with 3 times 25 ml of ethyl acetate. The extracts are dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 700 mg of crude oil. This oil is purified by elution in a 95/5 dichloromethane/methanol mixture at a flow rate of 10 ml/minute, on 20 g of silica, to give 39 mg of 3-{6-[4-(2-diisopropylaminoethylamino)-benzenesulfonyloxy]benzothiazol-2-ylcarbamoyl}azetidine-1-carboxylic acid tert-butyl ester.

후처리

  1. customThe solution obtained
  2. extractionthe reaction medium is extracted with 3 times 25 ml of ethyl acetate
  3. dry with materialThe extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give 700 mg of crude oil
  7. customThis oil is purified by elution in a 95/5 dichloromethane/methanol mixture at a flow rate of 10 ml/minute, on 20 g of silica

출처 및 근거

ORD 기록
ord-1276d23cd1814d6c8da2a8fbbefab2d8
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632952B2

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