Allyl chloroformate → HCID 68692451, compound

HRID 1991486Notes

Reaction equation

HRID 1991486 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[NH2:15])(C)(C)C.CCN(C(C)C)C(C)C.Cl[C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28]>C1COCC1>[CH2:30]([O:29][C:27](=[O:28])[NH:15][C:9]1[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=1[NH2:7])[CH:31]=[CH2:32]

Participants

5

Reactant 3

HCID 18052Allyl chloroformateHCID 81531DiisopropylethylamineHCID 24688763N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

Product 1

HCID 68692451HCID 68692451, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(2-Amino-4-fluoro-phenyl)-carbamic acid tert-butyl ester (5.0 g, 22 mmol, 1 equiv.) was added to a solution of DIPEA (3.62 ml, 22 mmol, 1 equiv.) in THF (80 ml). The mixture was cooled to 0° C. and allyl chloroformate (2.36 ml, 22 mmol, 1 equiv.) in THF added. The mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the crude extracted from ethylacetate and aq. NaHCO3. The residue was taken up in DCM and trifluoroacetic acid (1:1) for 2 hours. The product was obtained after evaporation of the organic solvents.

Workup

  1. customThe solvent was evaporated
  2. extractionthe crude extracted from ethylacetate and aq. NaHCO3
  3. waittrifluoroacetic acid (1:1) for 2 hours
  4. customThe product was obtained
  5. customafter evaporation of the organic solvents

Sources & evidence

ORD record
ord-56bc8e904a254d2384e10d1ee043afd2
Source dataset
uspto-grants-2010_01
Patent number
US07645785B2

Reaction notes

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