Sodium Sulfate → ethyl 4-{[1-(1-trityl-1H-imidazol-4-yl)propyl]amino}butanoate

HRID 1924261Notes

Reaction equation

HRID 1924261 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C([O-])(=O)C.[Na+].[C:16]([N:35]1[CH:39]=[C:38]([C:40](=O)[CH2:41][CH3:42])[N:37]=[CH:36]1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH3-]C#N.[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CO.CCOCC>[C:16]([N:35]1[CH:39]=[C:38]([CH:40]([NH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:41][CH3:42])[N:37]=[CH:36]1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 24436Sodium SulfateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 22285048HCID 22285048, compound

Product 1

HCID 53629165ethyl 4-{[1-(1-trityl-1H-imidazol-4-yl)propyl]amino}butanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

In a 100 ml, three-necked flask fitted with a magnetic stirrer, under inert atmosphere, ethyl 4-aminobutanoate hydrochloride a17 (1.75 g, 0.0104 mol) is dissolved in MeOH (30 ml). Sodium acetate (1.28 g, 0.0156 mol), a solution of 1-(1-trityl-1H-imidazol-4-yl)propan-1-one x89 (0.96 g, 2.6 mmol) in a mixture of MeOH (7 ml) and Et2O (20 ml), NaBH3CN (0.15 g, 2.34 mmol) and finally Na2SO4 are added. After stirring for 48 h at room temperature, the mixture is poured on Et2O/H2O. The organic phase is washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude ethyl 4-{[1-(1-trityl-H-imidazol-4-yl)propyl]amino}butanoate x90 (0.814 g) is used in the next step without any further purification.

Workup

  1. additionare added
  2. additionthe mixture is poured on Et2O/H2O
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude ethyl 4-{[1-(1-trityl-H-imidazol-4-yl)propyl]amino}butanoate x90 (0.814 g) is used in the next step without any further purification

Sources & evidence

ORD record
ord-e27ab0a0d0f14766b6ca0e706cabf425
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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