2-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide → HCID 46196300, compound

HRID 1188254Notes

Reaction equation

HRID 1188254 reaction equation
C([NH:8][CH:9]([CH:29]([CH3:32])[CH2:30][CH3:31])[C:10]([NH:12][CH:13]([C:18]1([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:21][CH2:20][CH2:19]1)[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O>[NH2:8][CH:9]([CH:29]([CH3:32])[CH2:30][CH3:31])[C:10]([NH:12][CH:13]([C:18]1([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[CH2:21][CH2:20][CH2:19]1)[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11]

Participants

3

Reactant 1

HCID 673857212-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide

Product 1

HCID 46196300HCID 46196300, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide (Example 2) was dissolved in CF3COOH. This solution was stirred at room temperature for 3 hours, and then evaporated under vacuum to remove CF3COOH. The produced white solid was collected, dissolved in anhydrous ethyl ether, and washed repeatedly with saturated sodium bicarbonate until pH of the eluate was neutral. This solution of ethyl ether was then washed with saturated sodium chloride for 2-3 times, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by column chromatography to give 2-amino-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide.

Workup

  1. customevaporated under vacuum
  2. customto remove CF3COOH
  3. customThe produced white solid was collected
  4. dissolutiondissolved in anhydrous ethyl ether
  5. washwashed repeatedly with saturated sodium bicarbonate until pH of the eluate
  6. washThis solution of ethyl ether was then washed with saturated sodium chloride for 2-3 times
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f95b36f22a9745db89e78c6cbf11b3cb
Source dataset
uspto-grants-2014_03
Patent number
US08673981B2

Reaction notes

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