Ethyl chloroformate → HCID 86700482, compound

HRID 1404839Notes

Reaction equation

HRID 1404839 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[NH2:22])([O-])=O.[Cl-].[NH4+].CCN(C(C)C)C(C)C.Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36]>CO.[Zn]>[NH2:22][C:5]1[C:6]([N+:19]([O-:21])=[O:20])=[C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:4]=1[NH:1][C:35](=[O:36])[O:37][CH2:38][CH3:39]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 86700480HCID 86700480, compound

Product 1

HCID 86700482HCID 86700482, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of compound 9 (1.5 g, 5 mmol, 1.00 equiv) in methanol (7 mL) is added zinc powder (1.64 g, 25 mmol, 5.00 equiv) followed by ammonium chloride solution (1.33 g, 25 mmol, 5.00 equiv) dropwise. After 5 h, DIPEA (0.806 g, 6.25 mmol, 1.25 equiv) and ethyl chloroformate (0.54 g, 5 mmol, 1.00 equiv) are added to reaction mixture at 10° C. and the stirring continued till consumption of starting material (by TLC). The reaction mixture is diluted with water (30 mL) and extracted in ethyl acetate (75 mL), dried using brine and over MgSO4. After concentration the crude material obtained is purified to afford the title compound.

Workup

  1. customthe stirring continued till consumption of starting material (by TLC)
  2. additionThe reaction mixture is diluted with water (30 mL)
  3. extractionextracted in ethyl acetate (75 mL)
  4. customdried
  5. concentrationAfter concentration the crude material
  6. customobtained
  7. customis purified

Sources & evidence

ORD record
ord-3de57f63c2cf4bbfa30fe7da69bcbf22
Source dataset
uspto-grants-2014_12
Patent number
US08916133B2

Reaction notes

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