Triethylammonium formate → (2R, 3S)-3-benzoylamino-1-chloro-2-hydroxy-4-phenylbutane

HRID 2180337Notes

Reaction equation

HRID 2180337 reaction equation
[C:1]([NH:9][C@@H:10]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11](=[O:14])[CH2:12][Cl:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=O.C(N(CC)CC)C>C(OCC)(=O)C.C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.Cl[Rh+]C1(C)C(C)=C(C)C(C)=C1C>[C:1]([NH:9][C@@H:10]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C@@H:11]([OH:14])[CH2:12][Cl:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11084032Triethylammonium formateHCID 13339657(3S)-3-Benzoylamino-1-chloro-4-phenyl-2-butanone

Product 1

HCID 11472194(2R, 3S)-3-benzoylamino-1-chloro-2-hydroxy-4-phenylbutaneYield 98.8%

Reagents, catalysts & solvents 2

HCID 178425932HCID 178425932, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3S)-3-Benzoylamino-1-chloro-4-phenyl-2-butanone (301.8 mg, 1.0 mmol) and a formic acid/triethylamine azeotropic mixture (0.2 ml) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.67 mg, 0.001 mmol, s/c=1000) in ethyl acetate (0.5 ml), followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography to afford a desired compound, (2R, 3S)-3-benzoylamino-1-chloro-2-hydroxy-4-phenylbutane (300.1 mg; yield: 98.8%). The production ratio of the desired (2R,3S)-form to the isomeric (2S,3S)-form, (2R,3S):(2S,3S), was 27.3:1. The results of elementary analysis were as follows.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0ef834aba0054b94a8b58f0ed2ec995e
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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