1,2-Dichloroethane → HCID 178499181, compound

HRID 1453882Notes

Reaction equation

HRID 1453882 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:18]([OH:20])=O)=[N:11][NH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=NC2N(O)N=NC=2C=1.[CH3:31][NH:32][CH2:33][C@@H:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[OH:35].C(N(CC)CC)C.C(Cl)CCl>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[N:12][NH:11][C:10]=1[C:18]([N:32]([CH2:33][C@H:34]([OH:35])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:31])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 6950649HalostachineHCID 57528495Methyl 4-benzyloxy-3-carboxy-1H-pyrazole-5-carboxylate

Product 1

HCID 178499181HCID 178499181, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-benzyloxy-3-carboxy-1H-pyrazole-5-carboxylate (1.5 g, 5.43 mmol; prepared as in Example 31, Step 1) in DMF (20 mL) were added HOAT (1.11 g, 8.15 mmol), (1R)-2-(methylamino)-1-phenylethanol (1.23 g, 8.15 mmol; prepared as described in Gurjar, M. K., et al., Org. Process Res. Dev. 1998, 2, 422.), triethylamine (0.82 g, 8.15 mmol), and EDC (1.56 g, 8.15 mmol). The reaction mixture was stirred at ambient temperature for 3 hours. The DMF was removed in vacuo and the residue was partitioned between saturated aqueous NH4Cl and EtOAc. The layers were separated and the aqueous was extracted twice more with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford the title product. ES MS (M+1)=410.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned between saturated aqueous NH4Cl and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous was extracted twice more with EtOAc
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-965f9976a6524d59ae52ffcd2b885b17
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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