Phenacyl bromide → HCID 117761577, compound

HRID 1474636Notes

Reaction equation

HRID 1474636 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH2:7][O:8]2)(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.Br[CH2:51][C:52]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:53]>C(#N)C.C(OC(=O)C)C>[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:30]=[CH:31][C:32]([O:35][CH2:51][C:52](=[O:53])[C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)=[CH:33][CH:34]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH2:7][O:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 81531DiisopropylethylamineHCID 86729324HCID 86729324, compound

Product 1

HCID 117761577HCID 117761577, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,2S,3S,4R,55)-1-(acetoxymethyl)-5-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (260 mg, 0.46 mmol) and DIPEA (0.38 mL, 2.25 mmol) in acetonitrile (2.25 mL), 2-bromo-1-phenylethanone (269 mg, 1.3 mmol) was added at r.t. and stirred overnight. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and washed with water (20 mL) and brine (20 mL) successively. The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 2.2:7.8 acetone:hexane) to afford the title compound (230 mg, 0.33 mmol, 73.6%).

Workup

  1. customAfter completion of the reaction
  2. washwashed with water (20 mL) and brine (20 mL) successively
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe volatiles were evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 2.2:7.8 acetone:hexane)

Sources & evidence

ORD record
ord-d636522e5e4a40058c4663b7c464ed62
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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