Diisopropylethylamine → 4-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-(8-tert-butoxycarbonylaminooctanoylamino)benzothiazol-6-yl ester

HRID 1867978ノート

反応式

HRID 1867978 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[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.[NH2:52][C:53]1[S:54][C:55]2[CH:61]=[C:60]([O:62][S:63]([C:66]3[CH:71]=[CH:70][C:69]([NH:72][CH2:73][CH2:74][N:75]([CH:79]([CH3:81])[CH3:80])[CH:76]([CH3:78])[CH3:77])=[CH:68][CH:67]=3)(=[O:65])=[O:64])[CH:59]=[CH:58][C:56]=2[N:57]=1>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:52][C:53]1[S:54][C:55]2[CH:61]=[C:60]([O:62][S:63]([C:66]3[CH:71]=[CH:70][C:69]([NH:72][CH2:73][CH2:74][N:75]([CH:79]([CH3:81])[CH3:80])[CH:76]([CH3:77])[CH3:78])=[CH:68][CH:67]=3)(=[O:65])=[O:64])[CH:59]=[CH:58][C:56]=2[N:57]=1)=[O:18])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 5462158-(((Tert-butoxy)carbonyl)amino)octanoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579808584-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-aminobenzothiazol-6-yl ester2 回

生成物 1

HCID 579808354-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-(8-tert-butoxycarbonylaminooctanoylamino)benzothiazol-6-yl ester収率 98.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

175 mg of 8-tert-butoxycarbonylaminooctanoic acid, 256 mg of HBTU and 235 μl of DIEA are added to a solution of 4-(2-diisopropylaminoethylamino)-benzenesulfonic acid 2-aminobenzothiazol-6-yl ester (intermediate 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 mixture 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 338 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 10 g of silica, to give 153 mg of 4-(2-diisopropylaminoethylamino)benzenesulfonic acid 2-(8-tert-butoxycarbonylaminooctanoylamino)benzothiazol-6-yl ester.

後処理

  1. customThe solution obtained
  2. extractionthe reaction mixture 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 338 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 10 g of silica

出典と根拠

ORDレコード
ord-a4678fc7c4864651ae8e5ef642d149ee
出典データセット
uspto-grants-2009_12
特許番号
US07632952B2

反応ノート

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