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

HRID 963965Notes

Reaction equation

HRID 963965 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-8a80c1ff47324876b11a6f28c0e859e9
Source dataset
uspto-grants-1998_06
Patent number
US05767088

Reaction notes

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