Water → HCID 67015452, compound

HRID 1470066Notes

Reaction equation

HRID 1470066 reaction equation
[NH2:1][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.CCN(C(C)C)C(C)C.O>CCOC(C)=O>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][C:15]([NH: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 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 67015452HCID 67015452, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

tert-Butyl 5-aminopentylcarbamate (2.02 g, 10 mmol) was dissolved in EtOAc, 4-nitrophenyl carbonochloridate (2.22 g, 11 mmol) was added, the mixture cooled on an icebath, DIEA (2.05 mL, 12 mmol) was added with stirring and the mixture gradually allowed to reach rt and stirred for 3 h. The mixture was transferred to a separatory funnel with EtOAc and H2O, and shaken. The organic phase was extracted with 1N HCl, H2O, 5% NA2CO3, H2O (three times), brine, dried over Mg2SO4, filtered and concentrated to yield compound 9.

Workup

  1. additionwas added
  2. customto reach rt
  3. stirringstirred for 3 h
  4. stirringshaken
  5. extractionThe organic phase was extracted with 1N HCl, H2O, 5% NA2CO3, H2O (three times), brine
  6. dry with materialdried over Mg2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-022b6b20a6254297a6979a04662a135d
Source dataset
uspto-grants-2015_04
Patent number
US09006426B2

Reaction notes

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