4-Methoxybenzenesulfonyl chloride → HCID 18678868, compound

HRID 1634701Notes

Reaction equation

HRID 1634701 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6][NH2:7])[CH3:2].C(N(CC)CC)C.[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>C(Cl)Cl>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:7]([S:47]([C:44]2[CH:43]=[CH:42][C:41]([O:40][CH3:39])=[CH:46][CH:45]=2)(=[O:49])=[O:48])[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:8])=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 77264-ChlorobenzaldehydeHCID 8471Triethylamine2×HCID 419889Ethyl 3-aminopropanoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18678868HCID 18678868, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of β-alanine ethyl ester (154 mg, 1 mmol) in anhydrous methylene chloride (7 mL) at room temperature was added triethyl amine (101 mg, 1 mmol) and 4-chlorobenzaldehyde (155 mg, 1.1 mmol). After being stirred for 0.5 h, sodium triacetoxyborohydride (318 mg, 1.5 mmol) was added and the reaction mixture was stirred for additional 1 h at room temperature, followed by the addition of 4-methoxybenzenesulfonyl chloride (207 mg, 1 mmol) and triethyl amine (152 mg, 1.5 mmol). The resulting mixture was stirred for 18 h, quenched with 10% citric acid (10 mL) and, after 30 min, extracted with methylene chloride (2×30 mL). Two phases was separated and the organic layers was washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography (2/1: hexanes/ethyl acetate) to give ethyl 3-[(4-chlorobenzyl)-(4-methoxybenzenesulfonyl)-amino]-propionate (44 mg, 0.1 mmol).

Workup

  1. stirringthe reaction mixture was stirred for additional 1 h at room temperature
  2. stirringThe resulting mixture was stirred for 18 h
  3. customquenched with 10% citric acid (10 mL) and, after 30 min
  4. extractionextracted with methylene chloride (2×30 mL)
  5. customTwo phases was separated
  6. washthe organic layers was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by silica gel chromatography (2/1: hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7c8b5b72639a4b32830ba985ad453fed
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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