Methyl 4-aminobenzoate → HCID 22105643, compound

HRID 1455976Notes

Reaction equation

HRID 1455976 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:10]=1[CH2:11][NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 22105647HCID 22105647, compound

Product 1

HCID 22105643HCID 22105643, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2-benzyloxy-5-methanesulphonylbenzaldehyde (10 g) and methyl 4-aminobenzoate (5.2 g) in toluene (100 mL) was heated on a steam bath for 18 hours and evaporated to dryness. The residue was dissolved in a mixture of methanol (100 mL) and tetrahydrofuran (100 mL) and the first portion of sodium borohydride (1.3 g) was added. The mixture was stirred for 1 hour and the second portion of sodium borohydride (1.3 g) was added. The mixture was stirred for 30 minutes and evaporated to dryness. The residue was dissolved in dichloromethane (250 mL) and was washed with water and dried (MgSO4). The solvent was evaporated and the residue subjected to chromatography on silica eluting initially with dichloromethane and then with a mixture of ethyl acetate and dichloromethane (3/7 v/v) to give methyl 4-[N-(2-benzyloxy-5-methanesulphonylbenzyl)amino]benzoate, yield 10.2 g, mp 124° C.

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in a mixture of methanol (100 mL) and tetrahydrofuran (100 mL)
  4. additionthe first portion of sodium borohydride (1.3 g) was added
  5. additionthe second portion of sodium borohydride (1.3 g) was added
  6. stirringThe mixture was stirred for 30 minutes
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in dichloromethane (250 mL)
  9. washwas washed with water
  10. dry with materialdried (MgSO4)
  11. customThe solvent was evaporated
  12. additionwith a mixture of ethyl acetate and dichloromethane (3/7 v/v)

Sources & evidence

ORD record
ord-d2488cb7b23b45fc9eb5ca018bedb859
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

Loading…