Ethyl bromoacetate → HCID 18442436, compound

HRID 458941Notes

Reaction equation

HRID 458941 reaction equation
[O:1]=[S:2]1(=[O:36])[C:8]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:7]=2[N:6]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:16][CH:15]=2)[CH2:5][C:4]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46]>CC#N.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:36]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:13][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:11]=[CH:12][C:7]=2[N:6]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[CH:18][CH:19]=2)[CH2:5][C:4]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:3]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18442437HCID 18442437, compound

Product 1

HCID 18442436HCID 18442436, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

1,1-Dioxo-3,3-dibutyl-5-(4-t-butoxycarbonylaminophenyl)-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine Method 107; 597 mg, 1.16 mmol) was dissolved in MeCN (20 ml), K2CO3 (480 mg, 3.5 mmol), tetrabutylammoniumbromide (54 mg, 0.17 mmol) and ethyl bromoacetate (167 μl, 1.5 mmol) was added. The mixture was heated to 60° C. overnight. The solvent was evaporated under reduced pressure. EtOAc and water was added and the water layer was extracted two times with EtOAc. The combined organic layer was washed once with brine, dried, filtered and evaporated under reduced pressure to give the title compound 0.617 g (89%). M/z 603.3.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionEtOAc and water was added
  3. extractionthe water layer was extracted two times with EtOAc
  4. washThe combined organic layer was washed once with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-42ced3ead2c6485f9a367f3cd04ef03e
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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