Tetrahydrofuran → HCID 554073, compound

HRID 1590354Notes

Reaction equation

HRID 1590354 reaction equation
C(O[CH:4]([S:6][CH2:7][C:8]([OH:10])=[O:9])[CH3:5])C.O[N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]1=[O:18].C1C[O:22][CH2:21][CH2:20]1>>[C:16]1(=[O:17])[N:12]([O:10][C:8](=[O:9])[CH2:7][S:6][CH2:4][CH2:5][O:22][CH2:21][CH3:20])[C:13](=[O:18])[CH2:14][CH2:15]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 80170N-HydroxysuccinimideHCID 10511223Acetic acid, [(1-ethoxyethyl)thio]-

Product 1

HCID 554073HCID 554073, compound

Procedure

The S-(1-ethoxyethyl)mercaptoacetic acid (5.76 g, 35.1 mmol) is combined with N-hydroxysuccinimide (4.85 g, 42.1 mmol) in 100 mL of anhydrous THF. To this is added a solution of 1,3-dicycloherylcarbodiimide (8.70 g, 42.1 mmol) in 65 mL of anhydrous THF. The mixture is stirred at room temperature for 2 hours, or until TLC analysis indicates complete formation of the succinimidyl ester. The mixture is then filtered, and the filtrate is concentrated in vacuo to a viscous residue. The residue is dissolved in ethyl acetate, washed with water, brine, and dried (MgSO4). Removal of the solvent leaves the crude succinimidyl ester as an oil, which is further purified by flash chromatography on silica gel, using ethyl acetate:hexanes as the column eluant, to give 5.1 g of S-1-ethoxyethylmercaptoacetic acid succinimidyl ester 8 as a colorless oil.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated in vacuo to a viscous residue
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent
  7. customleaves the crude succinimidyl ester as an oil, which
  8. customis further purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3e33ff8e6a75480fb0702d18ec244d02
Source dataset
uspto-grants-1993_04
Patent number
US05202451

Reaction notes

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