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

HRID 1867978Notes

Reaction equation

HRID 1867978 reaction equation
[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]

Participants

7

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a4678fc7c4864651ae8e5ef642d149ee
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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