tert-Butanol → Tert-butyl [4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridin-2-yl]carbamate

HRID 492844Notes

Reaction equation

HRID 492844 reaction equation
C([N:3]([CH2:6]C)CC)C.[CH2:8]([O:15][C:16]([NH:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26](C(O)=O)[CH:25]=2)=[CH:21][C:20]=1[F:35])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.C(OCC)(=O)C.[C:59]([OH:63])([CH3:62])([CH3:61])[CH3:60]>>[CH2:8]([O:15][C:16]([NH:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:3][C:6](=[O:43])[O:63][C:59]([CH3:62])([CH3:61])[CH3:60])[CH:25]=2)=[CH:21][C:20]=1[F:35])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 231530984-(4-Benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylic acid

Product 1

HCID 57677355Tert-butyl [4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridin-2-yl]carbamateYield 65.5%

Procedure

Triethylamine (4.6 ml) was added to a suspension of 4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylic acid (5.04 g) in tert-butanol (50 ml) at room temperature, and the mixture was stirred. After adding diphenylphosphoryl azide (3.13 ml) thereto at room temperature, the mixture was stirred for 30 minutes at room temperature under a nitrogen atmosphere. It was then heated and stirred at 90° C. for 30 minutes and at 100° C. for 4 hours. The reaction mixture was subsequently cooled to room temperature. Ethyl acetate (25 ml) was added thereto, and the reaction mixture was stirred for 30 minutes while cooling in an ice bath. The precipitated crystals were filtered and washed with diethyl ether. They were then subjected to aeration drying for 1 hour at room temperature to provide the title compound (3.92 g, 65.5%) as colorless crystals.

Workup

  1. stirringat room temperature, the mixture was stirred for 30 minutes at room temperature under a nitrogen atmosphere
  2. temperatureIt was then heated
  3. stirringstirred at 90° C. for 30 minutes and at 100° C. for 4 hours
  4. stirringthe reaction mixture was stirred for 30 minutes
  5. temperaturewhile cooling in an ice bath
  6. filtrationThe precipitated crystals were filtered
  7. washwashed with diethyl ether
  8. customdrying for 1 hour at room temperature

Sources & evidence

ORD record
ord-35b0b60eed054ae4a817432439b3c45e
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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