HCID 86614675, compound → HCID 86614674, compound

HRID 1433790Notes

Reaction equation

HRID 1433790 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:17](=[O:27])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)[C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])(C)(C)C>C(O)=O>[NH2:7][C@@H:8]([C@H:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:10])[C:17]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)=[O:27]

Participants

3

Reactant 1

HCID 86614675HCID 86614675, compound

Product 1

HCID 86614674HCID 86614674, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of [(1S,2S)-1-(4-ethynyl-phenylcarbamoyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester (300 mg, 0.79 mmol) in formic acid (5 mL) was heated to 50° C. for 1 hour. The reaction was concentrated in vacuo, basified with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to give (2S,3S)-2-amino-N-(4-ethynyl-phenyl)-3-phenyl-butyramide as a foam (214 mg, 92%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2b70a709dc441a484222121f544d237
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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