Hydrochloric Acid → 7-({Benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one

HRID 749247Notes

Reaction equation

C(=O)([O:10][C:11]1[C:16]2[NH:17][C:18](=[O:20])[S:19][C:15]=2[C:14]([C:21](=[O:24])[CH2:22]Br)=[CH:13][CH:12]=1)OCC1C=CC=CC=1.[CH2:26]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)C(C)C)(C)C.Cl>CN(C=O)C>[CH2:26]([N:33]([CH2:22][C:21]([C:14]1[C:15]2[S:19][C:18](=[O:20])[NH:17][C:16]=2[C:11]([OH:10])=[CH:12][CH:13]=1)=[O:24])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of benzyl 7-(bromoacetyl)-2-oxo-2,3-dihydro-1,3-benzothiazol-4-yl carbonate (50 mg) in dry DMF (1 ml) stirring under nitrogen was added N-benzyl-6-(4-phenylbutoxy)hexan-1-amine (Tetrahedron Letters. 1994, 35, 9375) (60 mg) and N,N-diisopropylethylamine (32 μl). After stirring at 40° C. for 2 h, 2N HCl was added and the mixture extracted with ethyl acetate. The solution was dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a 5 g silica SPE cartridge, eluting with a stepped gradient of 2% to 10% methanol-dichloromethane mixtures to give the title compound (50 mg). LCMS RT=3.14 min.

Workup

extractionthe mixture extracted with ethyl acetate
dry with materialThe solution was dried (MgSO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified on a 5 g silica SPE cartridge
washeluting with a stepped gradient of 2% to 10% methanol-dichloromethane mixtures

Sources & evidence

ORD record: ord-d2426491c0174ecb8d72e0597b94fd7b
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402598B2

Reaction notes

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