1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-1-Phenylethyl 2-bromo-2-phenylacetate

HRID 923434Notes

Reaction equation

HRID 923434 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[C:12]1([C@@H:18](O)[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(OCC)(=O)C>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([O:5][C@H:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:19])=[O:4]

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 97919Bromo(phenyl)acetic acidHCID 4431351-Phenylethanol, (S)-

Product 1

HCID 59166394(S)-1-Phenylethyl 2-bromo-2-phenylacetateYield 76%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of α-bromophenylacetic acid (11.20 g, 52.1 mmol), (S)-(−)-1-phenylethanol (8.2 mL, 67.9 mmol) and DMAP (0.63 g, 5.2 mmol) in CH2Cl2 (100 mL). was added EDAC (13.80 g, 72.0 mmol). The resulting mixture was stirred at room temperature for 3 hours then diluted with ethyl acetate (200 mL), washed with water (2×100 mL) and brine (100 mL). The organic layer was dried (MgSO4), filtered, and concentrated then purified by column chromatography to provide the title compound (12.6 g, 76% yield).

Workup

  1. washwashed with water (2×100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthen purified by column chromatography

Sources & evidence

ORD record
ord-ab7e73300a054e3683944bdf65351f86
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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