Hydrochloric Acid → 1,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

HRID 1383874Notes

Reaction equation

HRID 1383874 reaction equation
C(O[Al](OC(C)C)OC(C)C)(C)C.[C:14]([O:18][C:19](=[O:33])[NH:20][C@@H:21]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:22](=[O:25])[CH2:23][Cl:24])([CH3:17])([CH3:16])[CH3:15].Cl>C1(C)C=CC=CC=1>[C:14]([O:18][C:19](=[O:33])[NH:20][C@@H:21]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C@H:22]([OH:25])[CH2:23][Cl:24])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9926241tert-butyl N-((2S)-4-chloro-3-oxo-1-phenylbutan-2-yl)carbamateHCID 16685055Aluminum tri-iso-propoxide

Product 1

HCID 71466451,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Triisopropoxyaluminum (200 mg, 0.98 mmol) was diluted with 6 ml of toluene. Thereto was added 285 mg (0.96 mmol) of [1(S)-benzyl-2-oxo-3-chloropropyl]carbamic acid t-butyl ester, and the mixture was stirred at 25° C. for 16 hours. After hydrolysis with 1N hydrochloric acid, the reaction mixture was extracted with ethyl acetate. The solution obtained was analyzed quantitatively by HPLC under the same conditions as used in Example 1 and the yields and selectivity were calculated.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe solution obtained
  3. customthe yields

Sources & evidence

ORD record
ord-70af8e39c6c441aea21ced92e0355690
Source dataset
uspto-grants-2001_07
Patent number
US06255522B1

Reaction notes

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