Dimethylformamide → N-(tert-butoxycarbonyl)-L-alanyl-L-valinamide

HRID 1062905Notes

Reaction equation

HRID 1062905 reaction equation
[C:1]([O:5]N[C@H](C(O)=O)C)([CH3:4])([CH3:3])[CH3:2].C1C=C[C:15]2N(O)N=[N:18][C:16]=2[CH:17]=1.CN1C[CH2:27][O:26]CC1.Cl.[NH2:30][C@H:31]([C:35]([NH2:37])=[O:36])[CH:32]([CH3:34])[CH3:33].CN(C=[O:42])C>C(Cl)CCl>[C:1]([O:5][C:27]([NH:18][C@H:16]([C:17]([NH:30][C@H:31]([C:35]([NH2:37])=[O:36])[CH:32]([CH3:34])[CH3:33])=[O:42])[CH3:15])=[O:26])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 13689583L-Valinamide--hydrogen chloride (1/1)HCID 13714013N-tert-Butoxyalanine

Product 1

HCID 86589158N-(tert-butoxycarbonyl)-L-alanyl-L-valinamideYield 74%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

N-tert-Butoxyalanine (0.95 g, 5.0 mmol), EDC (1.0 g, 5.2 mmol), and HOBT (0.70 g, 5.2 mmol) are stirred in 10 mL of dry DMF under nitrogen for 1 h. N-Methylmorpholine (1.6 mL, 14.5 mmol) is added to L-valinamide hydrochloride (0.76 g, 5.0 mmol) in 7 mL of DMF, and the resulting suspension is agitated for 5-10 min and then added to the EDC mixture. The reaction mixture is stirred for 3 days. It is quenched with 1 N KHSO4 and extracted into ethyl acetate. The organic phase is washed successively with 1 N KHSO4, 1N NaHCO3, water, and brine, and dried with Na2SO4. Concentration and trituration with pentane affords the title compound as a white solid (1.07 g, 3.7 mmol, 74%). MS (CI) m/z 288 (MH+). HRMS (ESI) calcd for C13H25N3O4+H1 288.1923, found 288.1922.

Workup

  1. stirringThe reaction mixture is stirred for 3 days
  2. customIt is quenched with 1 N KHSO4
  3. extractionextracted into ethyl acetate
  4. washThe organic phase is washed successively with 1 N KHSO4, 1N NaHCO3, water, and brine
  5. dry with materialdried with Na2SO4
  6. concentrationConcentration and trituration with pentane

Sources & evidence

ORD record
ord-6119fb4198e1455aa38ad5484a0a2a97
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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