Tetrahydrofuran → Tert-butyl [4-(naphthalen-2-ylmethyl)-5-oxoperhydro-1,4-thiazepin-6-yl]carbamate

HRID 1986545Notes

Reaction equation

HRID 1986545 reaction equation
[H-].[Na+].C1COCC1.[O:8]=[C:9]1[CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][S:13][CH2:12][CH2:11][NH:10]1.Br[CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1>O.CCOC(C)=O>[CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[CH2:25][N:10]1[C:9](=[O:8])[CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH2:14][S:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 15591256(Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) ester

Product 1

HCID 57722245Tert-butyl [4-(naphthalen-2-ylmethyl)-5-oxoperhydro-1,4-thiazepin-6-yl]carbamateYield 191.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

81 mg of sodium hydride as a 60% suspension in oil (2.03 μmol) are introduced at room temperature into a 25 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 20 ml of THF and 500 mg of 26 (2.03 mmol). The medium is stirred for 1 hour and 449 mg (2.03 mmol) of 2-(bromomethyl)naphthalene are then added. The medium is stirred for 16 hours, 20 ml of EtOAc and 20 ml of water are added to the reaction medium and, after separation of the phases by settling, the organic phase is washed with 10 ml of water. The organic phase is dried, filtered and then evaporated to dryness to give 1.5 g of crude product, which product is chromatographed on a silica cartridge (25 g) with a 90/10 heptane/EtOAc mixture. 510 mg of product 42 are recovered (yield=65%).

Workup

  1. stirringThe medium is stirred for 1 hour
  2. stirringThe medium is stirred for 16 hours
  3. customafter separation of the phases
  4. washthe organic phase is washed with 10 ml of water
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-dfe430abacff43e18a4b20be84dad106
Source dataset
uspto-grants-2009_06
Patent number
US07550453B2

Reaction notes

Loading…