Benzoyl chloride → 2,6-di-(N-benzoyl)amino-3-hydroxyheptanedioic acid, diethyl ester

HRID 568967Notes

Reaction equation

HRID 568967 reaction equation
[NH2:1][CH:2]([CH:8]([OH:26])[CH2:9][CH2:10][CH:11]([NH:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(CC)CC.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[C:34]([NH:1][CH:2]([CH:8]([OH:26])[CH2:9][CH2:10][CH:11]([NH:17][C:18](=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 140975952-amino-3-hydroxy-6-(N-benzoyl)aminoheptanedioic acid, diethyl ester

Product 1

HCID 140975962,6-di-(N-benzoyl)amino-3-hydroxyheptanedioic acid, diethyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Amine (9) (4.0 g, 10.9 mM) is taken up in CH2Cl2 (150 ml), cooled in an ice bath, and treated with Et3N (1.67 ml, 12 mM). Benzoyl chloride (1.27 ml, 10.9 mM) is added slowly over a period of 5 minutes and stirring continued at 4° C. for 1 hour. The reaction is warmed to room temperature and stirred overnight. This mixture is washed with 5% aqueous HCl (3×100 ml), saturated aqueous NaCl (3×100 ml), dried over anhydrous MgSO4, filtered and evaporated to dryness in vacuo to yield a white foam. The latter is purified by flash chromatography on silica gel eluting with 12% acetone/CH2Cl2 to yield 3.0 g (59% yield) of the desired product as a white foam. 'H-N.M.R. (CDCl3 /TMS): δ=1.19 (t, 3H, --CH2CH3); 1.22 (t, 3H, --CH2CH3); 1.40-2.27 (m, 4H, --CH2CH2 --); 4.19 (2q, 4H, --CH2CH3); 4.00-5.00 (4H, 10H, 2>CHCO2Et, CHOH); 6.90-7.86 ppm (m, 12H, 2NH and 2Ph).

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred overnight
  3. washThis mixture is washed with 5% aqueous HCl (3×100 ml), saturated aqueous NaCl (3×100 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customto yield a white foam
  8. customThe latter is purified by flash chromatography on silica gel eluting with 12% acetone/CH2Cl2

Sources & evidence

ORD record
ord-8c41092dd00b4ab8a6ee5684b6a32cc4
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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