Phenacyl bromide → HCID 14308410, compound

HRID 1393997Notes

Reaction equation

HRID 1393997 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]>CCOC(C)=O>[CH2:17]([O:7][C:6](=[O:8])[C@H:2]([C@@H:3]([CH3:5])[OH:4])[NH:1][C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 2724766N-tert-Butoxycarbonyl-L-threonine

Product 1

HCID 14308410HCID 14308410, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

To a stirred suspension of Boc-Thr-OH (21.91 g, 0.1 mol) in EtOAc (200 ml) at 0° C., TEA (14 ml, 0.1 mol) and bromoacetophenone (19.0 g, 0.1 mol) were added. The reaction mixture was allowed to warm to 20° C., stirred for 2 days and then diluted with EtOAc (500 ml). After washing successively with aq HCl (200 ml, 0.1 N), H2O (100 ml), aq NaBCO3 (200 ml, 1 N) and brine (200 ml), drying (Na2SO4), filtered and concentrated in vacuo, the residue was triturated with Et2O and filtered. The resulting solid was dried in the dark to yield D3 (28.6 g, 85%). Rf=0.55 (hex-EtOAc 1:1, silica); M.p.=114.2° C.; [α]D22 −29.4 (c 2, EtOAc).

Workup

  1. washAfter washing successively with aq HCl (200 ml, 0.1 N), H2O (100 ml), aq NaBCO3 (200 ml, 1 N) and brine (200 ml)
  2. dry with materialdrying (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customthe residue was triturated with Et2O
  6. filtrationfiltered
  7. customThe resulting solid was dried in the dark

Sources & evidence

ORD record
ord-4978044b56df48d38ad747e709bf0ff0
Source dataset
uspto-grants-2008_03
Patent number
US07348310B2

Reaction notes

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