Diethylamine → HCID 28814207, compound

HRID 423077Notes

Reaction equation

HRID 423077 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].CS(O[CH2:11][CH2:12][C@H:13]([NH:21]C(OC(C)(C)C)=O)[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)(=O)=O>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C@@H:13]([NH2:21])[CH2:12][CH2:11][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 57750320(S)-3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propyl methanesulfonate2×

Product 1

HCID 28814207HCID 28814207, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

Diethylamine (0.426 mL, 4.12 mmol) and (S)-3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propyl methanesulfonate (Intermediate 59) (500 mg, 1.37 mmol) were dissolved in THF (10 mL) and sealed into a microwave tube. The reaction was heated to 120° C. for 50 minutes in the microwave reactor and cooled to room temperature. The reaction mixture was concentrated and diluted with DCM (5 mL). TFA (1 mL) was added and the reaction was stirred at 20° C. for 1 hour. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 3.5N ammonia/MeOH and pure fractions were evaporated to dryness to afford (S)-1-(4-chlorophenyl)-N3,N3-diethylpropane-1,3-diamine (119 mg, 36.0%) as a yellow oil.

Workup

  1. customsealed into a microwave tube
  2. temperaturecooled to room temperature
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with DCM (5 mL)
  5. additionTFA (1 mL) was added
  6. customThe crude product was purified by ion exchange chromatography
  7. washThe desired product was eluted from the column
  8. customwere evaporated to dryness

Sources & evidence

ORD record
ord-77e2bee07dfe4735a093d72eb1214788
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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