Boc-leu-chloromethylketone → (2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-5-methylhexane

HRID 2180343Notes

Reaction equation

HRID 2180343 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:10](=[O:13])[CH2:11][Cl:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].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]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C@H:10]([OH:13])[CH2:11][Cl:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 7020822Boc-leu-chloromethylketoneHCID 11084032Triethylammonium formate

Product 1

HCID 86592058(2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-5-methylhexaneYield 96.4%

Reagents, catalysts & solvents 2

HCID 178425931HCID 178425931, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3S)-3-tert-Butoxycarbonylamino-1-chloro-5-methyl-2-hexanone (263.8 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, 0.0001 mmol, s/c=1000) in ethyl acetate (1.0 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, (2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-5-methylhexane (255.8 mg; yield: 96.4%). As a result of HPLC analysis, the production ratio of the desired (2S,3S)-form to the isomeric (2R,3S)-form, (2S,3S):(2R,3S), was 7.7:1. 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-d48cde9cc4924a3fa903d2751f9ad974
Source dataset
uspto-grants-2005_05
Patent number
US06888012B2

Reaction notes

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