Diethylamine → tert-butyl (2S)-3,3-dimethyl-2-{3-[(1-methyl-1H-benzimidazol-2-yl)methyl]-2-oxo-1-imidazolidinyl}butanoate

HRID 1174218Notes

Reaction equation

HRID 1174218 reaction equation
C1C2C(CO[C:16]([N:18]([CH2:34][C:35]3[N:39]([CH3:40])[C:38]4[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=4[N:36]=3)[CH2:19][CH2:20][NH:21][C@@H:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:17])C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C.C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)OC1C=CC([N+]([O-])=O)=CC=1>CN(C)C=O.ClCCCl>[CH3:31][C:30]([CH3:32])([CH3:33])[C@H:22]([N:21]1[CH2:20][CH2:19][N:18]([CH2:34][C:35]2[N:39]([CH3:40])[C:38]3[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=3[N:36]=2)[C:16]1=[O:17])[C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 78756Bis(4-nitrophenyl) carbonateHCID 67406495tert-butyl(2S)-2-[(2-{[(9H-fluoren-9-ylmethoxy)carbonyl][(1-methyl-1H-benzimidazol-2-yl)methyl]amino}ethyl)amino]-3,3-dimethylbutanoate

Product 1

HCID 67406119tert-butyl (2S)-3,3-dimethyl-2-{3-[(1-methyl-1H-benzimidazol-2-yl)methyl]-2-oxo-1-imidazolidinyl}butanoateYield 64%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 59D (0.19 g) in N,N-dimethylformamide (3.5 mL) was treated with diethylamine (0.35 mL), stirred at 25° C. for 1.5 hours and concentrated. A solution of the residue in 1,2-dichloroethane (7 mL) was treated with bis-(p-nitrophenyl) carbonate (0.128 g, 1.2 eq.), stirred at 60° C. for 16 hours and concentrated. The residue was chromatographed on silica gel, eluting with ethyl acetate:dichloromethane (3:2) to give 80 mg (64% yield) of the title compound.

Workup

  1. concentrationconcentrated
  2. stirringstirred at 60° C. for 16 hours
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel
  5. washeluting with ethyl acetate:dichloromethane (3:2)

Sources & evidence

ORD record
ord-94759f6d530b49d7bded3432a8b7ff1f
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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