5-Fluoro-2-nitrophenol → [3-tert-Butoxycarbonylamino-2-(5-fluoro-2-nitro-phenoxy)-propyl]-carbamic acid tert-butyl ester

HRID 532262Notes

Reaction equation

HRID 532262 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].[C:12]([O:16][C:17](=[O:31])[NH:18][CH2:19][CH:20](O)[CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C>C1COCC1>[C:12]([O:16][C:17](=[O:31])[NH:18][CH2:19][CH:20]([O:11][C:5]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH3:14])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 375632tert-butyl N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}carbamate

Product 1

HCID 58413396[3-tert-Butoxycarbonylamino-2-(5-fluoro-2-nitro-phenoxy)-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Nitro-5-fluorophenol (8.4 g) and (3-tert-butoxycarbonylamino-2-hydroxy-propyl)-carbamic acid tert-butyl ester (17.0 g) were dissolved in THF (60 ml) and triphenylphosphine (21 g) and di-tert-butyl-azodicarboxylate (18.4 g) were added. The exothermic reaction was cooled in an ice bath. Then the mixture was stirred at room temperature overnight. It was concentrated in vacuo and the residue was dissolved in dichloromethane, washed with water and 1M NaOH. The organic layer was dried and concentrated in vacuo. The residue was purified by chromatography (silica/dichloromethane:methanol 25:1).

Workup

  1. customThe exothermic reaction
  2. temperaturewas cooled in an ice bath
  3. concentrationIt was concentrated in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water and 1M NaOH
  6. customThe organic layer was dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography (silica/dichloromethane:methanol 25:1)

Sources & evidence

ORD record
ord-2e231f6655ce4ad196f008e04915a65d
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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