1,1'-Carbonyldiimidazole → {2-[4-(2-Butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonylamino]-2-oxoethyl}carbamic acid t-butyl ester

HRID 1888349Notes

Reaction equation

HRID 1888349 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:25]([C:29]1[N:30]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([S:44]([NH2:47])(=[O:46])=[O:45])=[CH:40][CH:39]=2)[C:31]([CH:35]=[O:36])=[C:32]([Cl:34])[N:33]=1)[CH2:26][CH2:27][CH3:28].C1CCN2C(=NCCC2)CC1>C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][C:10]([NH:47][S:44]([C:41]1[CH:42]=[CH:43][C:38]([CH2:37][N:30]2[C:31]([CH:35]=[O:36])=[C:32]([Cl:34])[N:33]=[C:29]2[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:39][CH:40]=1)(=[O:46])=[O:45])=[O:12])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 579314034-(2-Butyl-4-chloro-5-formyl-imidazol-1-ylmethyl)benzenesulfonamide

Product 1

HCID 57931394{2-[4-(2-Butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonylamino]-2-oxoethyl}carbamic acid t-butyl esterYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

N-Boc-glycine (2.8 g, 16 mmol, 1.0 eq) was dissolved into 50 mL THF. CDI (2.6 g, 16 mmol, 1.0 eq) was added, and the mixture heated to 80° C. for 2 hours. The solution was cooled to room temperature and added to a solution of intermediate (2c) (5.7 g, 16 mmol, 1.0 eq) in 100 mL THF followed by DBU (2.4 mL, 16 mmol, 1.0 eq). The mixture was stirred at room temperature overnight. The mixture was then concentrated, redissolved into 100 mL EtOAc, washed with saturated bicarbonate, saturated aqueous NaCl, dried over MgSO4, and evaporated. The residue was chromatographed (10% MeOH:EtOAc with 0.7% NH3) to yield intermediate (2d) (5.6 g).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationThe mixture was then concentrated
  3. dissolutionredissolved into 100 mL EtOAc
  4. washwashed with saturated bicarbonate, saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was chromatographed (10% MeOH:EtOAc with 0.7% NH3)

Sources & evidence

ORD record
ord-053b33ef57e6449cbee39ec92eff3574
Source dataset
uspto-grants-2013_08
Patent number
US08501798B2

Reaction notes

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