Benzyl Alcohol → HCID 23566488, compound

HRID 397310Notes

Reaction equation

HRID 397310 reaction equation
[CH2:1]([C@H:5]([N:9]1[C@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:11]([N:21]2[C@@H:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:24][O:23][C:22]2=[O:32])[C:10]1=[O:33])[C:6]([OH:8])=[O:7])[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.ClC(O[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=O.C(O)C1C=CC=CC=1>ClCCl>[CH2:1]([C@H:5]([N:9]1[C@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:11]([N:21]2[C@@H:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:24][O:23][C:22]2=[O:32])[C:10]1=[O:33])[C:6]([O:8][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 23566482HCID 23566482, compound

Product 1

HCID 23566488HCID 23566488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.79 gm (1.76 mMol) 2-(S)-isobutyl-2-[3(S)-(4(S)-phenyloxazolidin-2-on-3-yl)-4(R)-(2-(phenyl)ethyl)azetidin-2-on-1-yl]acetic acid in 20 mL dichloromethane was cooled to −4° C. To this solution were added 0.26 mL (1.85 mMol) triethylamine followed by 0.26 mL (1.85 mMol) benzyl chloroformate. After 5 minutes 0.20 mL (1.93 mMol) benzyl alcohol were added and the reaction mixture was allowed to warm to room temperature over 1 hour. The reaction mixture was then washed sequentially with two portions each of 1 N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The remaining organics were dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 1:1 hexane: ethyl acetate to provide the title compound as a colorless, crystalline solid.

Workup

  1. washThe reaction mixture was then washed sequentially with two portions each of 1 N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialThe remaining organics were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washeluting with 1:1 hexane

Sources & evidence

ORD record
ord-19eade8207f741e38e0c157fce80e66e
Source dataset
uspto-grants-2003_08
Patent number
US06610680B1

Reaction notes

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