tert-Butyl carbazate → HCID 66839551, compound

HRID 546771Notes

Reaction equation

HRID 546771 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4]/[C:5](=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]2)=[C:12]([O:22][CH3:23])[CH:11]=1)/[C:6](O)=[O:7].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(C(C)C)CC)(C)C.C(OC(C)(C)C)(=O)[NH:49][NH2:50]>ClCCl.C(OCC)(=O)C.O>[Cl:1][CH2:2][CH2:3][CH2:4]/[C:5](=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]2)=[C:12]([O:22][CH3:23])[CH:11]=1)/[C:6]([NH:49][NH2:50])=[O:7]

Participants

8

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 58528693HCID 58528693, compound

Product 1

HCID 66839551HCID 66839551, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-2-[1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene]pentanoic acid (CAS No. 870843-27-9, 10 g) was dissolved in dichloromethane (130 mL). BOPCl (4.53 g), IPEA (12.3 g) and tert-butyl carbazate (2.82 g) were added and the reaction solution was stirred at room temperature for three hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with a 1 N sodium hydroxide solution and 1 N hydrochloric acid in this order. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. A solution of 4 N hydrochloric acid in ethyl acetate (100 mL) was added to the residue, and the reaction solution was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure to obtain 3.87 g of a crude product of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with a 1 N sodium hydroxide solution and 1 N hydrochloric acid in this order
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionA solution of 4 N hydrochloric acid in ethyl acetate (100 mL) was added to the residue
  6. stirringthe reaction solution was stirred at room temperature for two hours
  7. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-69a780d942354a269d8b09140546ff6f
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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