Hydrochloric Acid → N-[2-(Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)ethyl]-3-[2-(2-phenylethoxy)ethylaminosulphonyl]propanamide
Reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][NH:12][S:13]([CH2:16][CH2:17][C:18]([OH:20])=O)(=[O:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O[C:23]1[C:28]2[NH:29][C:30](=[O:32])[S:31][C:27]=2[CH:26]=[CH:25][CH:24]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)[N:42]1CC[CH2:44][CH2:43]1.C(N(C(C)C)CC)(C)C.Cl.CN(C)C=[O:70]>>[OH:70][N:29]1[C:28]2[CH:23]=[CH:24][CH:25]=[C:26]([CH2:44][CH2:43][NH:42][C:18](=[O:20])[CH2:17][CH2:16][S:13]([NH:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:14])=[O:15])[C:27]=2[S:31][C:30]1=[O:32]Participants
7
Reactant 6
Product 1
Conditions
- Temperature
- -15 °C
Procedure
A solution of the product from step b) (3.89 g), 7-2-aminoethyl)4-hydroxy-1,3-benzothiazol-2(3H)-one hydrochloride (3.22 g), bromotripyrrolidinophosphonium hexafluorophosphate, PyBroP, (6.32 g) in dimethylformamide (50 ml) was cooled to -15° C. and diisopropylethylamine (9.0 ml) was added dropwise over 5 minutes. The solution was stirred at -15° C. for 5 min then allowed to warm to 13° C. over 4 hours. This mixture was then added dropwise over 40 min to dilute hydrochloric acid (2N, 500 ml) and after stirring over the weekend the solid was collected by filtration. This solid was dried in vacuo to give the subtitle compound (4.5 g).
Workup
- temperatureto warm to 13° C. over 4 hours
- stirringafter stirring over the weekend the solid
- filtrationwas collected by filtration
- customThis solid was dried in vacuo
Sources & evidence
- ORD record
- ord-adfb7b5e8e17413a913a00b7880a3751
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05973167
Reaction notes
Loading…