1,1'-Carbonyldiimidazole → HCID 10853285, compound

HRID 2393104Notes

Reaction equation

HRID 2393104 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]([O:17][C:18]([NH:20][C@@H:21]([C:25]([OH:27])=O)[CH:22]([CH3:24])[CH3:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C.[CH2:37]([O:44][NH2:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[CH3:24][CH:22]([CH3:23])[C@@H:21]([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:14])([CH3:15])[CH3:16])[C:25]([NH:45][O:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:27]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 102313O-BenzylhydroxylamineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 10853285HCID 10853285, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CDI (2.45 g, 15.1 mmol) is added to a solution of N-(tert-butoxycarbonyl)-D-valine (3.28 g, 15.1 mmol) and CH2Cl2 (60 mL). The solution is stirred for 1 hour at room temperature. Diisopropylethylamine (2.90 mL, 16.6 mmol) and O-benzylhydroxylamine (2.64 g, 16.5 mmol) are added and the solution stirred for 16 hours at room temperature. The solution is concentrated, diluted with EtOAc, and washed with 5% HCl (2×50 mL), NaHCO3 (50 mL) and brine (50 mL). The organic solution is dried (MgSO4), filtered, and concentrated to give 4.42 g (91%) of the title compound as a white solid which is carried on crude.

Workup

  1. stirringthe solution stirred for 16 hours at room temperature
  2. concentrationThe solution is concentrated
  3. additiondiluted with EtOAc
  4. washwashed with 5% HCl (2×50 mL), NaHCO3 (50 mL) and brine (50 mL)
  5. dry with materialThe organic solution is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b703a5ba778f4e989d12e299aa085327
Source dataset
uspto-grants-1998_09
Patent number
US05804593

Reaction notes

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