Benzyl Alcohol → HCID 10521181, compound

HRID 842425Notes

Reaction equation

HRID 842425 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:15])=[CH:17][CH:18]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Product 1

HCID 10521181HCID 10521181, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(N-Boc-aminomethyl)benzoic acid (500 mg, 1.99 mmol), DMAP (catalytic amount), benzyl alcohol (226 μl, 2.19 mmol) and dichloromethane (20 ml) was added dicyclohexylcarbodiimide (1M solution in dichloromethane, 2.19 ml, 2.19 mmol) and the mixture stirred at room temperature for 60 hours. The precipitate was removed by filtration and the filtrate concentrated in vacuo. Diethyl ether (50 ml) was added to the residue, the resulting precipitate removed by filtration and the filtrate concentrated in vacuo. Purification by flash column chromatography (petrol/EtOAc, 3:1) gave the title compound (412 mg, 61%) as a solid.

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. additionDiethyl ether (50 ml) was added to the residue
  4. customthe resulting precipitate removed by filtration
  5. concentrationthe filtrate concentrated in vacuo
  6. customPurification by flash column chromatography (petrol/EtOAc, 3:1)

Sources & evidence

ORD record
ord-59a1821b40304ea9bd1dd87c2006630e
Source dataset
uspto-grants-2002_04
Patent number
US06375926B1

Reaction notes

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