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

HRID 2043621Notes

Reaction equation

HRID 2043621 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].N1C=C(CN2CC(C3C=CC=CC=3)CC2=O)N2C=CC=CC=12.C([O-])(=O)C.[Na+].[C:38]([N:57]1[CH:61]=[C:60]([C:62](=O)[CH2:63][CH3:64])[N:59]=[CH:58]1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[BH3-]C#N.[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CO.CCOCC>[C:38]([N:57]1[CH:61]=[C:60]([CH:62]([NH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:63][CH3:64])[N:59]=[CH:58]1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

9

Reactant 6

HCID 24436Sodium SulfateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 159524532-Pyrrolidinone,1-(imidazo[1,2-a]pyridin-3-ylmethyl)-4-phenyl-HCID 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 al 7 (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-1H-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-1H-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-de4e2494ac3747cb91ea884cc8e0867a
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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