Isobutylamine → HCID 28519069, compound

HRID 852568Notes

Reaction equation

HRID 852568 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][S:15][CH3:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.[CH2:47]([NH2:51])[CH:48]([CH3:50])[CH3:49]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH:51][CH2:47][CH:48]([CH3:50])[CH3:49])[CH2:13][CH2:14][S:15][CH3:16])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 6558IsobutylamineHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 89857Boc-L-methionineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 28519069HCID 28519069, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-tert-butoxycarbonylamino-4-methylsulfanyl-butyric acid (D95) (2.0 g, 8.0 mmol, 1 equiv), EDAC.HCl (1.84 g, 9.6 mmol, 1.2 equiv), HOBT (1.47 g, 9.6 mmol, 1.2 equiv), 4-ethylmorpholine (1.76 g, 16 mmol, 2 equiv) and iso-butylamine (952 ml, 9.6 mmol, 1.2 equiv) in CH2Cl2 (10 ml) were stirred at room temperature for 16 h. The solution was concentrated in vacuo and the residue dissolved in AcOEt. The organic phase was washed with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo to give ((S)-1-isobutylcarbamoyl-3-methylsulfanyl-propyl)-carbamic acid tert-butyl ester (D96) (2.38 g, 98%) as a colourless oil.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue dissolved in AcOEt
  3. washThe organic phase was washed with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e2e9ca76a7a43dab459ec4c70bb4c5e
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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