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

HRID 2180338Notes

Reaction equation

HRID 2180338 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 11347236(2S, 3S)-3-benzoylamino-1-chloro-2-hydroxy-4phenylbutaneYield 97.3%

Reagents, catalysts & solvents 2

HCID 178425931HCID 178425931, 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) (1S,2S)-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. Quantitative analysis by HPLC revealed production of a desired compound, (2S, 3S)-3-benzoylamino-1-chloro-2-hydroxy-4-phenylbutane (295.6 mg; yield: 97.3%). The production ratio of the desired (2S,3S)-form to the isomeric (2R,3S)-form, (2S,3S):(2R,3S), was 22.6:1. The results of elementary analysis were as follows.

Sources & evidence

ORD record
ord-eeefe79ddda6494bb3f336593e2e8e89
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

Loading…