Hydrochloric Acid → N-[2-(4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)ethyl]-3-[2-(2-phenylethoxy)ethylaminosulphonyl]propanamide

HRID 1422274Notes

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.[NH2:22][CH2:23][CH2:24][C:25]1[C:33]2[S:32][C:31](=[O:34])[NH:30][C:29]=2[C:28]([OH:35])=[CH:27][CH:26]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(C(C)C)CC)(C)C.Cl>CN(C)C=O>[OH:35][C:28]1[C:29]2[NH:30][C:31](=[O:34])[S:32][C:33]=2[C:25]([CH2:24][CH2:23][NH:22][C:18](=[O:20])[CH2:17][CH2:16][S:13]([NH:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:14])=[O:15])=[CH:26][CH:27]=1

Participants

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-059fe89040bc469cb3cd9282c02b0a2f
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080869

Reaction notes

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