3-{6-[4-(2-Diisopropylaminoethylamino)benzenesulfonyloxy]benzothiazol-2-yl-carbamoyl}azetidine-1-carboxylic acid tert-butyl ester → 4-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-(8-aminooctanoylamino)-benzothiazol-6-yl ester

HRID 1867979Notes

Reaction equation

HRID 1867979 reaction equation
C(OC(N1[CH2:11][CH:10]([C:12](=[O:43])[NH:13][C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([NH:33][CH2:34][CH2:35][N:36]([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[CH:20]=[CH:19][C:17]=3[N:18]=2)C1)=O)(C)(C)C>O1CCOCC1>[NH2:18][CH2:17][CH2:16][CH2:22][CH2:21][CH2:20][CH2:11][CH2:10][C:12]([NH:13][C:14]1[S:15][C:16]2[CH:22]=[C:21]([O:23][S:24]([C:27]3[CH:28]=[CH:29][C:30]([NH:33][CH2:34][CH2:35][N:36]([CH:37]([CH3:38])[CH3:39])[CH:40]([CH3:42])[CH3:41])=[CH:31][CH:32]=3)(=[O:26])=[O:25])[CH:20]=[CH:19][C:17]=2[N:18]=1)=[O:43]

Participants

3

Reactant 1

HCID 579808573-{6-[4-(2-Diisopropylaminoethylamino)benzenesulfonyloxy]benzothiazol-2-yl-carbamoyl}azetidine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 115779044-(2-Diisopropylaminoethylamino)benzenesulfonic acid 2-(8-aminooctanoylamino)-benzothiazol-6-yl esterYield 212.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3 ml of hydrochloric dioxane are added to a solution of 153 mg of 3-{6-[4-(2-diisopropylaminoethylamino)benzenesulfonyloxy]benzothiazol-2-yl-carbamoyl}azetidine-1-carboxylic acid tert-butyl ester (intermediate 36) in 3 ml of dioxane. The resulting solution is stirred for 5 hours at room temperature and then evaporated under reduced pressure to give 152 mg of 4-(2-diisopropylaminoethylamino)benzenesulfonic acid 2-(8-aminooctanoylamino)-benzothiazol-6-yl ester.

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6555cfee2db44cbf8671b1a7be813451
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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