Dicyclohexylcarbodiimide → Methyl 8-(Boc-amino)-octanoate

HRID 975792Notes

Reaction equation

HRID 975792 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:19]1CCC(N=C=NC2CCCCC2)CC1>CO>[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 5462158-(((Tert-butoxy)carbonyl)amino)octanoic acid

Product 1

HCID 130187773Methyl 8-(Boc-amino)-octanoateYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BocNH(CH2)7CO2H (prepared, Example 8, Step 1) (300 mg, 1.2 mmol) was dissolved in methanol (5 mL) and DCC (239 mg, 1.2 mmol) was then added. The solution was stirred at room temperature overnight. The DCU was removed by filtration and the solvent was removed in vacuo. The residue was then taken up in EtoAc and washed with dilute HCl (200 mL×3), water (200 mL×3), and then dried over MgSO4, filtered, and the solvent was removed in vacuo to yield an oil, 0.259 g (79% yield);

Workup

  1. customThe DCU was removed by filtration
  2. customthe solvent was removed in vacuo
  3. washwashed with dilute HCl (200 mL×3), water (200 mL×3)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customto yield an oil, 0.259 g (79% yield)

Sources & evidence

ORD record
ord-e39aaf1e6658456e926d5b8e55b18cde
Source dataset
uspto-grants-1997_03
Patent number
US05610145

Reaction notes

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