Chlorotrimethylsilane → HCID 57030967, compound

HRID 1941621Notes

Reaction equation

HRID 1941621 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([SH:8])[CH2:5][N:4]1[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10].C(N(CC)CC)C.C[Si](C)(C)Cl.[S:27](Cl)(=[O:30])(=[O:29])[NH2:28]>ClCCl>[CH2:12]([O:11][C:9]([N:4]1[CH2:5][C@@H:6]([SH:8])[CH2:7][C@H:3]1[CH2:2][NH:1][S:27](=[O:30])(=[O:29])[NH2:28])=[O:10])[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine3×HCID 24499Chlorosulfamic acidHCID 572801191-Pyrrolidinecarboxylic acid, 2-(aminomethyl)-4-mercapto-, 2-propenyl ester, (2S-cis)-

Product 1

HCID 57030967HCID 57030967, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S,4S)-2-aminomethyl-1-allyloxycarbonyl-4-mercaptopyrrolidine (2.80 g: ca. 13.14 mmole) in dichloromethane (66 ml) at -50° C., triethylamine (4.02 ml: 28.91 mmole) and trimethylchlorosilane (3.76 ml: 28.91 mmole) are added dropwise over 15 minutes. The mixture is stirred at the same temperature for 20 minutes. To the reaction mixture triethylamine (0.92 ml: 6.57 mmole) and a solution of sulfamoyl chloride (19.37 mmole) in dichloromethane (6.8 ml) are added dropwise over 20 minutes at -70° C., and the mixture is stirred for 30 minutes. To the reaction mixture triethylamine (3.84 ml: 27.59 mmole) is again added over 1 hour at -50° C. The reaction mixture is kept at the same temperature overnight and concentrated in vacuo. The residual oil is purified by silica gel chromatography (ethyl acetate) to give (2S,4S)-1-allyloxycarbonyl-2-(sulfamoylamino)methyl-4-mercaptopyrrolidine (2.64 g). Yield: 68%. White powder.

Workup

  1. stirringthe mixture is stirred for 30 minutes
  2. customis kept at the same temperature overnight
  3. concentrationconcentrated in vacuo
  4. customThe residual oil is purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-c99f35b21b7e4d59aefb947166b9e627
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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