Ethyl bromoacetate → HCID 46862036, compound

HRID 242486Notes

Reaction equation

HRID 242486 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[C@H:3]([NH:8][C:9]([N:11]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][C:14]=2[C:13]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=2[F:28])=[N:12]1)=[O:10])[C:4]([NH:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.Br[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]>C(#N)C>[CH3:1][C:2]([CH3:30])([CH3:29])[C@H:3]([NH:8][C:9]([N:11]1[C:19]2[CH2:18][CH2:17][N:16]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:15][C:14]=2[C:13]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=2[F:28])=[N:12]1)=[O:10])[C:4]([NH:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 46862777HCID 46862777, compound

Product 1

HCID 46862036HCID 46862036, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of intermediate 84 (0.39 g), DIEA (0.35 mL) and ethyl bromoacetate (0.22 mL) in acetonitrile was heated at 60° C. for 1.5 h. After evaporation of MeCN, the residue was extracted between EtOAc and saturated sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography with 70% to 90% EtOAc/Hex to give compound 83 (0.27 g, 57%). LCMS (+ESI) m/z=510.3 [M+H]+.

Workup

  1. customAfter evaporation of MeCN
  2. extractionthe residue was extracted between EtOAc and saturated sodium bicarbonate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product was purified by column chromatography with 70% to 90% EtOAc/Hex

Sources & evidence

ORD record
ord-77b04465baeb44578f2224bd1a01e109
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Reaction notes

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