Nalpha-Tosyl-L-phenylalanine chloromethyl ketone → (2R, 3S)-3-(p-toluenesulfonyl)amino-1-chloro-2-hydroxy-4-phenylbutane

HRID 2180335Notes

Reaction equation

HRID 2180335 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@@H:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:15])[CH2:13][Cl:14])(=[O:9])=[O:8])=[CH:3][CH:2]=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]1([CH3:23])[CH:2]=[CH:3][C:4]([S:7]([NH:10][C@@H:11]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:12]([OH:15])[CH2:13][Cl:14])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 439647Nalpha-Tosyl-L-phenylalanine chloromethyl ketoneHCID 11084032Triethylammonium formate

Product 1

HCID 11187332(2R, 3S)-3-(p-toluenesulfonyl)amino-1-chloro-2-hydroxy-4-phenylbutaneYield 98.3%

Reagents, catalysts & solvents 2

HCID 178425932HCID 178425932, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3S)-3-(p-Toluenesulfonyl)amino-1-chloro-4-phenyl-2-butanone (175.9 mg, 0.5 mmol) and a formic acid/triethylamine azeotropic mixture (0.1 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=500) 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 give a desired compound, (2R, 3S)-3-(p-toluenesulfonyl)amino-1-chloro-2-hydroxy-4-phenylbutane (173.5 mg; yield: 98.3%). HPLC analysis revealed that the production ratio of the desired (2R,3S)-form to the isomeric (2S,3S)-form, (2R,3S):(2S,3S), was 10.9:1. 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-b8b9af19b3bf43c5942f43dfd6a5c6b6
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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