Phenacyl bromide → HCID 118260110, compound

HRID 1779166Notes

Reaction equation

HRID 1779166 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:26][C:27]([C@H:29]([C@@:47]([OH:59])([CH2:55][C:56]([O-:58])=[O:57])[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])/[CH:30]=[CH:31]/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:28])[C:14]([O:16][CH2:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].Br[CH2:61][C:62]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:63].CCN(CC)CC>C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:26][C:27]([C@H:29]([C@@:47]([OH:59])([CH2:55][C:56]([O:58][CH2:61][C:62](=[O:63])[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)=[O:57])[C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])/[CH:30]=[CH:31]/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:28])[C:14]([O:16][CH2:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 131734848HCID 131734848, compound

Product 1

HCID 118260110HCID 118260110, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1-tert-Butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-(2-oxo-2-phenyl-ethoxycarbonyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (88.3 mg) was dissolved in ethyl acetate (5 mL), and a commercially available reagent of 2-bromoacetophenone (32 mg) and Et3N (24 μL) were added. The mixture was stirred at room temperature for 18 hours. To the reaction solution was added ethyl acetate and the mixture was washed with water and a saturated brine in this order. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The product was purified by silica gel chromatography (Megabondelute was used, elution solvent 20%-40% ethyl acetate/n-hexane) to obtain 56.6 mg (56%) of the title compound (LCMS m/z 937 (M+1) Rt 3.80 min.).

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe product was purified by silica gel chromatography (Megabondelute was used, elution solvent 20%-40% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-132ba56b8b794ea28c06eecfc4adfcfb
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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