(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → HCID 59570099, compound

HRID 2071178Notes

Reaction equation

HRID 2071178 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([N:11]([CH3:13])[CH3:12])[CH:10]=1)[O:6][CH2+:7].[O:14]1[CH2:16][C@@H:15]1[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:13][N:11]([CH3:12])[C:9]1[CH:10]=[C:3]([CH:4]=[C:5]([O:6][CH3:7])[CH:8]=1)[CH2:2][NH:1][CH2:16][C@@H:15]([OH:14])[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutaneHCID 178477761HCID 178477761, compound

Product 1

HCID 59570099HCID 59570099, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

(3-(aminomethyl)-5-(dimethylamino)phenoxy)methylium (0.0361 g, 0.2 mmol, 1.2 eq) was dissolved in the minimum amount of anhydrous CH2Cl2 under Ar. tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (0.0439 g, 0.167 mmol, 1 eq) was added with stirring. Anhydrous CH2Cl2 was added dropwise until all of the epoxide had dissolved. The reaction was heated to 50° C. After heating overnight all of the solvent was gone leaving a solid in the flask. Purification via flash chromatography yielded 0.0405 g, (0.091 mmol, 54% yield) of the product.

Workup

  1. dissolutionhad dissolved
  2. temperatureAfter heating overnight all of the solvent
  3. customwas gone leaving a solid in the flask
  4. customPurification via flash chromatography

Sources & evidence

ORD record
ord-10d1a9508caf4afda6f97ccdaff122d1
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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