Benzoyl chloride → HCID 178445561, compound

HRID 1857547Notes

Reaction equation

HRID 1857547 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[CH:10]([CH2:15][PH:16]([O:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:28])[CH:10]([CH2:15][PH:16]([O:18][CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:26]=1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 178445560HCID 178445560, compound

Product 1

HCID 178445561HCID 178445561, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-[(4-Aminobenzyl)methoxyphosphinoylmethyl]4-methylpentanoic acid benzyl ester (230 mg, 0.57 mmole), benzoyl chloride (96 mg, 0.68 mmole), and triethylamine (69 mg, 0.68 mmole) were combined in cold (ice bath) chloroform (10 ml). After stirring for 1 hour at ice bath temperature the reaction mixture was diluted with chloroform (150 ml) and washed with water (20 ml), 1N hydrochloric acid (2×20 ml) and saturated sodium bicarbonate solution (2×20 ml) and dried with magnesium sulfate. After filtration and concentration the yellow residue was chromatographed (ethyl acetate) to give 190 mg (66%) of 2-[(4-Benzoylaminobenzyl)methoxy phosphinoylmethyl]4-methylpentanoic acid benzyl ester as a light yellow oil.

Workup

  1. washwashed with water (20 ml), 1N hydrochloric acid (2×20 ml) and saturated sodium bicarbonate solution (2×20 ml)
  2. dry with materialdried with magnesium sulfate
  3. filtrationAfter filtration and concentration the yellow residue
  4. customwas chromatographed (ethyl acetate)

Sources & evidence

ORD record
ord-90665177b4de4fe29f96a84ce376bfc7
Source dataset
uspto-grants-2000_11
Patent number
US06147061

Reaction notes

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