3,4-dihydro-2H-pyran → 4-(Benzyloxy)-7-{(1R)-2-bromo-1-[tetrahydro-2H-pyran-2-yloxy]ethyl}-1,3-benzothiazol-2(3H)-one

HRID 749243Notes

Reaction equation

HRID 749243 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:18])[S:17][C:13]=2[C:12]([C@@H:19]([OH:22])[CH2:20][Br:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:40]1[CH:45]=[CH:44][CH2:43][CH2:42][CH2:41]1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:18])[S:17][C:13]=2[C:12]([C@@H:19]([O:22][CH:41]2[CH2:42][CH2:43][CH2:44][CH2:45][O:40]2)[CH2:20][Br:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 689265704-(Benzyloxy)-7-[(1R)-2-bromo-1-hydroxyethyl]-1,3-benzothiazol-2(3H)-one

Product 1

HCID 693192914-(Benzyloxy)-7-{(1R)-2-bromo-1-[tetrahydro-2H-pyran-2-yloxy]ethyl}-1,3-benzothiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(benzyloxy)-7-[(1R)-2-bromo-1-hydroxyethyl]-1,3-benzothiazol-2(3H)-one (31 mg) in dry DCM (5 ml) under nitrogen, was added pyridinium p-toluenesulphonate (5 mg), followed by 3,4-dihydro-2H-pyran (30 μl). The mixture was evaporated in vacuo after 18 h and purified on a 2 g silica SPE cartridge, eluting with a stepped gradient 10% to 100% DCM-cyclohexane mixtures, to give the title compound (42 mg). LCMS RT=3.72 and 3.78 min.

Workup

  1. customThe mixture was evaporated in vacuo after 18 h
  2. custompurified on a 2 g silica SPE cartridge
  3. washeluting with a stepped gradient 10% to 100% DCM-cyclohexane mixtures

Sources & evidence

ORD record
ord-b3f72a61eb944a70a5d9da7854141211
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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