Ethyl bromoacetate → HCID 18442441, compound

HRID 458943Notes

Reaction equation

HRID 458943 reaction equation
[O:1]=[S:2]1(=[O:30])[C:8]2[CH:9]=[C:10](O)[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][C:4]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3]1.BrC[C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>CC#N.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:1]=[S:2]1(=[O:30])[C:8]2[CH:9]=[C:10]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][C:4]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 18442442HCID 18442442, compound

Product 1

HCID 18442441HCID 18442441, compoundYield 106.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-methylthio-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 26; 12.85 g, 28.71 mmol) in MeCN (150 ml) was added ethyl bromoacetate (3.85 ml, 34.6 mmol), tetrabutylammonium bromide (0.925 g, 2.869 mmol) and sodium carbonate (12.85 g, 121.2 mmol). The mixture was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was partitioned between DCM and 0.5 M HCl. The organic layer was washed with brine, dried (MgSO4) and concentrated. Chromatography using DCM/EtOAc (9:1) as eluent gave the desired product (15.45 g) as a tan oil. NMR 0.70–0.85 (m, 6H), 1.00–1.55 (m, 15H), 2.15 (s, 3H), 3.10 (s, 2H), 3.70 (bs, 2H), 4.25 (q, 2H), 4.70 (s, 2H), 6.65 (s, 1H), 6.90–7.30 (m, 6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between DCM and 0.5 M HCl
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6145cec9f7184ce68059aa596fdd56e7
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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