Chlorotrimethylsilane → HCID 57061306, compound

HRID 1034495Notes

Reaction equation

HRID 1034495 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([SH:13])[CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C[Si](C)(C)Cl.[S:28](Cl)(=[O:31])(=[O:30])[NH2:29]>ClCCl.Cl.CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([SH:13])[CH2:10][C@H:9]1[CH2:14][NH:15][S:28](=[O:31])(=[O:30])[NH2:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine2×HCID 24499Chlorosulfamic acidHCID 57228294HCID 57228294, compound

Product 1

HCID 57061306HCID 57061306, compoundYield 69%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of crude (2S,4S)-1-t-butoxycarbonyl-2-aminomethyl-4-mercaptopyrrolidine (4.1 g) in dichloromethane (250 ml) at -70° C. under a stream of nitrogen, triethylamine (8.87 ml) and trimethylchlorosilane (6.73 ml) are added. The mixture is stirred for 1 hour and 40 minutes, mixed with triethylamine (8.87 ml) and a solution of 1M-sulfamoyl chloride in dichloromethane (64 ml), and stirred for 1 hour. The reaction mixture is acidified with dilute hydrochloric acid. The organic layer is taken, diluted with 1N-hydrochloric acid (21 ml) and methanol (50 ml), stirred for 35 minutes at room temperature, and poured into water. The organic layer is taken, washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give (2S,4S)-1-t-butoxycarbonyl-2-sulfamoylaminomethyl-4-mercaptopyrrolidine (4.57 g). Yield: 69%. Colorless syrup. NMR δ(CDCl3) ppm: 1.46(s, 9H), 1.5 to 1.8(m, 1H), 1.71(d, J=6.6 Hz, 1H), 2.5 to 2.67(m, 1H), 3.0 to 3.46(m, 4H), 3.85 to 4.2(m, 2H), 4.6 (br s, 2H). IR ν (CHCl3) cm-1 : 3420, 3340, 3270, 1679.

Workup

  1. stirringstirred for 35 minutes at room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-80d1c46f724d4d74b1a6c2e5e5b65449
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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