Benzoyl chloride → HCID 18464184, compound

HRID 2230027Notes

Reaction equation

HRID 2230027 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:29])[CH:5]([CH2:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[NH:6][C:7](=[O:21])[CH2:8][N:9]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:10].C(N(CC)CC)C.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)(Cl)Cl.Cl>[CH3:2][O:3][C:4](=[O:29])[CH:5]([CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:25][CH2:24]1)[NH:6][C:7](=[O:21])[CH2:8][N:9]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:10]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 69461032HCID 69461032, compound

Product 1

HCID 18464184HCID 18464184, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent

Procedure

N-(Toluene4-sulfonyl)sarcosyl-β-(piperidin-4-yl)-D,L-alanine methyl ester hydrochloride (see Preparative Example C (109)) (65 mg, 0.15 mmol) was dissolved in CHCl3 (3 mL) and cooled in an ice bath. Triethylamine (61 μL) and benzoyl chloride (21 mg, 0.15 mmol) were added and the mixture was stirred for 1 hr. The mixture was diluted with 1N HCl (20 mL) and extracted with EtOAc (2×25 mL). The extracts were dried (Na2SO4), filtered and evaporated in vacuo to give a residue which was purified by silica gel flash chromatography (95:5 CH2Cl2/MeOH) to yield N-(toluene4-sulfonyl)sarcosyl-β-(N-benzoylpiperidin-4-yl)-D,L-alanine methyl ester (67 mg, 89%). The title compound was prepared via hydrolysis of the methyl ester using LiOH in THF/water (71 mg, 100%).

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with EtOAc (2×25 mL)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a residue which
  7. customwas purified by silica gel flash chromatography (95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-14a20b9d266b44f3bc26e3ca07b0c2bb
Source dataset
uspto-grants-2002_07
Patent number
US06423688B1

Reaction notes

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