Chlorotrimethylsilane → HCID 131714071, compound

HRID 1154689Notes

Reaction equation

HRID 1154689 reaction equation
[NH2:1][CH:2]([C:9]([OH:11])=[O:10])[CH2:3][CH2:4][S:5](=[O:8])([OH:7])=[O:6].[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13].[CH3:19][Si:20]([CH3:23])([CH3:22])Cl>C1C=CC=CC=1>[CH2:12]([NH+:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13].[CH3:19][Si:20]([CH3:23])([CH3:22])[NH:1][CH:2]([C:9]([O:11][Si:20]([CH3:23])([CH3:22])[CH3:19])=[O:10])[CH2:3][CH2:4][S:5](=[O:7])([OH:8])=[O:6]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 921172-Amino-4-sulfobutanoic acid

Product 1

HCID 131714071HCID 131714071, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of D,L-homocysteic acid (915 mg, 5 mmoles) in dry benzene (25 ml) is treated with triethylamine (2 g, 20 mmoles) and trimethylchlorosilane (2.5 ml, 2.16 g, 20 mmoles). After being stirred at room temperature for 42 hr, the mixture is quickly suction filtered to remove the triethylamine hydrochloride, and the filtrate is evaporated to dryness under reduced pressure to obtain N,O-bis(trimethylsilyl)-D,L-homocysteic acid triethylammonium salt as a pale amber-colored oil or soft semisolid (1.93 g, 90 percent yield). This product is kept protected from atmospheric moisture and used without further purification in the next step.

Workup

  1. filtrationthe mixture is quickly suction filtered
  2. customto remove the triethylamine hydrochloride
  3. customthe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6fdd74a94c8a45aaa2ae43e9c078a4d9
Source dataset
uspto-grants-1984_12
Patent number
US04490529

Reaction notes

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