Water → tert-Butyl (5-(((4-nitrophenoxy)carbonyl)oxy)pentyl)carbamate

HRID 1470065Notes

Reaction equation

HRID 1470065 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[C:15](Cl)(=[O:26])[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C.O>CCOC(C)=O>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][C:15]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:26])=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 44561365-(Boc-amino)-1-pentanol

Product 1

HCID 70654531tert-Butyl (5-(((4-nitrophenoxy)carbonyl)oxy)pentyl)carbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

tert-Butyl 5-hydroxypentylcarbamate (950 mg, 4.67 mmol) was dissolved in EtOAc, 4-nitrophenyl carbonochloridate (1.130 g, 5.14 mmol) was added, the mixture cooled on an icebath, triethylamine (0.85 mL, 6.07 mmol) was added with stirring and the mixture gradually allowed to reach rt and stirred overnight. The mixture was transferred to a separatory funnel with EtOAc and H2O, and shaken. The organic phase was extracted with 1N HCl, H2O, NAHCO3 (aq., sat.), H2O (twice), brine, dried over Mg2SO4, filtered and concentrated. The residue was purified by chromatography (mixtures of petroleum ether and EtOAc) to afford compound 1.

Workup

  1. additionwas added
  2. customto reach rt
  3. stirringstirred overnight
  4. stirringshaken
  5. extractionThe organic phase was extracted with 1N HCl, H2O, NAHCO3 (aq., sat.), H2O (twice), brine
  6. dry with materialdried over Mg2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography (mixtures of petroleum ether and EtOAc)

Sources & evidence

ORD record
ord-1980b86cb76d438dbc67e43f32017522
Source dataset
uspto-grants-2015_04
Patent number
US09006426B2

Reaction notes

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