Triethylamine → [1-[[(1H-Benzimidazol-2-ylmethyl)amino]carbonyl]-2-methylbutyl]carbamic acid 1,1-dimethylethyl ester

HRID 22609

Reaction equation

HRID 22609 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.Cl.Cl.[NH2:20][CH2:21][C:22]1[NH:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[CH3:4][C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:14]([NH:20][CH2:21][C:22]1[NH:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)=[O:16])[CH:10]([CH3:11])[CH2:12][CH3:13])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 145819Benzimidazol-2-ylmethylamine dihydrochloride hydrateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Product 1

HCID 67747066[1-[[(1H-Benzimidazol-2-ylmethyl)amino]carbonyl]-2-methylbutyl]carbamic acid 1,1-dimethylethyl esterYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature solution of 0.505 g N-(tert-butoxycarbonyl)-L-isoleucine in 10 ml of methylene chloride is added, in the following order, 0.50 g of 2-(aminomethyl)benzimidazole dihydrochloride hydrate, 1.07 g of BOP and 0.850 g of triethylamine. The reaction is stirred at room temperature for 2 hours, diluted with methylene chloride, and washed with saturated sodium chloride. The organic layer is dried, filtered, and concentrated in vacuo. Purification by chromatography (silica gel; 70% ethyl acetate/hexane) gives 0.669 g of the desired product.

Workup

  1. washwashed with saturated sodium chloride
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (silica gel; 70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b2ebf4b4fc064d1fb082620a179a8a10
Source dataset
uspto-grants-1995_06
Patent number
US05428167

Linked notes

Loading…