4-Chlorobenzenesulfonyl chloride → HCID 3330873, compound

HRID 1393513Notes

Reaction equation

HRID 1393513 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([NH2:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[CH:4]([NH:12][S:28]([C:25]1[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=1)(=[O:30])=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 75737DL-Phenylalanine, methyl ester

Product 1

HCID 3330873HCID 3330873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-3-phenyl-propionic acid methyl ester is dissolved in 25 mL of methylene chloride and the reaction charged with triethylamine (0.97 mL, 7 mmol) and 4-chlorobenzenesulfonylchloride at 0° C. The reaction is allowed to warm to room temperature (rt) and stirred overnight. The reaction is quenched with sodium bicarbonate, extracted with methylene chloride, dried over sodium sulfate, and concentrated in vacuo. The resultant solid is triturated with 20% ethylacetate/hexanes to provide the title compound. 13C NMR (100 MHz, CDCl3) 39.5, 52.8, 57.1, 127.5, 128.8, 128.9, 129.5, 129.6, 135.1, 138.4, 139.4, 171.5. MS 354.1 m/z (M+1).

Workup

  1. customThe reaction is quenched with sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant solid is triturated with 20% ethylacetate/hexanes

Sources & evidence

ORD record
ord-6d6c028172d04f26a837c343bc1eeeff
Source dataset
uspto-grants-2008_03
Patent number
US07345095B2

Reaction notes

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