Benzaldehyde → HCID 18464161, compound

HRID 2230026Notes

Reaction equation

HRID 2230026 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].[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[BH3-]C#N.[Na+].Cl>CO.C1COCC1.C([O-])(O)=O.[Na+].C(N(CC)CC)C>[CH3:2][O:3][C:4](=[O:29])[CH:5]([CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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

9

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 69461032HCID 69461032, compound

Product 1

HCID 18464161HCID 18464161, compoundYield 52.1%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-(Toluene-4-sulfonyl)sarcosyl-β-(piperidin-4-yl)-D,L-alanine methyl ester hydrochloride (180 mg, 0.402 mmol) was dissolved in MeOH (3 mL). Triethylamine (56 μL), benzaldehyde (53 mg, 0.502 mmol) and 1.0 M NaBH3CN in THF (400 μL) were added and the mixture was stirred for 5 hr. 1N HCl (3 mL) was added and the mixture was stirred for 5 minutes before diluting with saturated aqueous NaHCO3 (30 mL). The mixture was extracted with EtOAc (3×25 mL) and the combined extracts were dried (Na2SO4), filtered and evaporated in vacuo to give a residue which was purified by silica gel flash chromatography (95:5:0.5 CH2Cl2/MeOH/NH4OH) to give N-(toluene-4-sulfonyl)sarcosyl-β-(N-benzylpiperidin-4-yl)-D,L-alanine methyl ester (105 mg, 52%). The title compound was prepared via hydrolysis of the methyl ester using 0.5 N aqueous NaOH in THF/water as a very hygroscopic solid.

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. extractionThe mixture was extracted with EtOAc (3×25 mL)
  3. dry with materialthe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a residue which
  7. customwas purified by silica gel flash chromatography (95:5:0.5 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-f37f1c60a8694d1d8a5ab3940b0a2270
Source dataset
uspto-grants-2002_07
Patent number
US06423688B1

Reaction notes

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