Chlorotrimethylsilane → HCID 57786504, compound

HRID 253595Notes

Reaction equation

HRID 253595 reaction equation
[NH2:1][C@@H:2]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C@@H:3]([OH:15])[CH2:4][NH:5][C:6](=[O:14])[O:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.Cl[Si:31]([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C@@H:3]([O:15][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH2:4][NH:5][C:6](=[O:14])[O:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 57462031HCID 57462031, compound

Product 1

HCID 57786504HCID 57786504, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(trimethylsilyl)ethyl (2S,3S)-3-amino-4-cyclohexyl-2-hydroxybutylcarbamate (0.18 g, 0.54 mmol) in anhydrous CH2Cl2 (1.5 mL) at 0° C., triethylamine (0.41 mL, 2.70 mmol) was added, followed by chlorotrimethylsilane (176 mg, 1.62 mmol). The resulting white mixture was warmed to rt slowly, and stirred at rt for another 40 min. Solvent was removed under vacuum, and the residue was redissolved in anhydrous CH2Cl2 (1 mL), and evaporated to dryness under vacuum to give 2-(trimethylsilyl)ethyl (2S,3S)-3-amino-4-cyclohexyl-2-(trimethylsilyloxy)butylcarbamate (quant.) as a white solid; MS m/z 403 (M+H+).

Workup

  1. customSolvent was removed under vacuum
  2. dissolutionthe residue was redissolved in anhydrous CH2Cl2 (1 mL)
  3. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-6ccfe3fa3154445688434b41a20deea8
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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