Ethyl bromoacetate → HCID 18442431, compound

HRID 458935Notes

Reaction equation

HRID 458935 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O:8]=[S:9]1(=[O:38])[C:15]2[CH:16]=[C:17]([OH:22])[C:18]([S:20][CH3:21])=[CH:19][C:14]=2[N:13]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:12][C:11]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10]1.C([O-])([O-])=O.[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[O:38]=[S:9]1(=[O:8])[C:15]2[CH:16]=[C:17]([O:22][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:18]([S:20][CH3:21])=[CH:19][C:14]=2[N:13]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:12][C:11]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 18442432HCID 18442432, compound

Product 1

HCID 18442431HCID 18442431, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

Ethyl bromoacetate (0.101 g, 0.604 mmol) was added to a mixture of 1,1-dioxo-3,3-dibutyl-5-(4-chlorophenyl)-7-methylthio-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 99; 0.194 g, 0.402 mmol), anhydrous Na2CO3 (0.192 g, 1.81 mmol) and tetrabutylammonium bromide in MeCN (5 ml). The reaction mixture was refluxed for 3.5 hours. The solvent was evaporated under reduced pressure and the residue was extracted with DCM/water. The organic layer was separated, dried and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM/EtOAc (100:5 and 100:10) as eluent to give the title compound 0.197 g (86%). NMR (300 MHz) 0.80–0.89 (m, 6H), 1.0–1.45 (m, 15H), 2.34 (s, 3H), 3.16 (s, 2H), 3.68 (s, 2H), 4.30 (q, 2H), 4.71 (s, 2H), 7.05–7.11 (m, 3H), 7.19 (s, 1H), 7.29–7.35 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3.5 hours
  2. customThe solvent was evaporated under reduced pressure
  3. extractionthe residue was extracted with DCM/water
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-26caf6b1ff64436aac8021b90530e917
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

Loading…