Benzyl Bromide → Benzyl 6-(tert-butoxycarbonylamino)hexanoate

HRID 965540Notes

Reaction equation

HRID 965540 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]([O:24][C:25]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:26])([CH3:23])([CH3:22])[CH3:21]>C(Cl)Cl>[C:20]([O:24][C:25]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:34])=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acid

Product 1

HCID 12160267Benzyl 6-(tert-butoxycarbonylamino)hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.94 ml of DBU and then 1.54 ml of benzyl bromide are added at RT to a solution of 3 g of 6-(tert-butoxycarbonylamino)hexanoic acid in 60 ml of DCM and the mixture is stirred for 24 hours at RT. It is concentrated under vacuum, the residue is taken up with 100 ml of water and extracted with AcOEt, the organic phase is washed with a 5% solution of potassium carbonate, with a saturated solution of NaCl and with water and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 2.8 g of the expected product, which is used as such.

Workup

  1. concentrationIt is concentrated under vacuum
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed with a 5% solution of potassium carbonate, with a saturated solution of NaCl and with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-9492381d0f7946da95db8e310fbc0d90
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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