Phthalimide → 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylamino]benzothiazole

HRID 375168Notes

Reaction equation

HRID 375168 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:12])[CH2:10]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(=O)[NH:17]C(=O)C2=CC=CC=C12.O.NN.Cl[C:28]1[S:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1.C(N(CC)CC)C>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][NH:17][C:28]1[S:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6809PhthalimideHCID 8471TriethylamineHCID 119872-ChlorobenzothiazoleHCID 24654Hydrazine hydrate (1:1)HCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 536913712-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylamino]benzothiazoleYield 10%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

2-[(R)-N-tertobutyloxycarbonylamino]-1-propylamine was prepared by standard synthetic steps from (R)-2-(N-tert-butyloxycarbonylamino)-1-propanol by Mitsunobu reaction with phthalimide followed by reaction with hydrazine hydrate. This amine (0.52 g, 3.0 mmol) and 2-chlorobenzothiazole (0.76 g, 4.5 mmol) were dissolved in dioxan (20 ml) and triethylamine (0.83 ml, 6.0 mmol) was introduced. The reaction mixture was heated at 50° C. for 18 h, evaporated and purified by "flash" column chromatography, eluting with heptane/ethyl acetate (10:3) to provide the 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylamino]benzothiazole (0.09 g, 10%) as an oil, TLC Rf 0.31 [SiO2 ; hexane/ethyl acetate (10:3)].

Workup

  1. customevaporated
  2. custompurified by "flash" column chromatography
  3. washeluting with heptane/ethyl acetate (10:3)

Sources & evidence

ORD record
ord-fd80e7ff29954a10b24baead48906930
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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