Tetrahydrofuran → HCID 554073, compound

HRID 1452006Notes

Reaction equation

HRID 1452006 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].C1(N=C=NC2CCCCC2)CCCCC1.C1C[O:37][CH2:36][CH2:35]1>>[C:16]1(=[O:17])[N:12]([O:10][C:8](=[O:9])[CH2:7][S:6][CH2:4][CH2:5][O:37][CH2:36][CH3:35])[C:13](=[O:18])[CH2:14][CH2:15]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10868DicyclohexylcarbodiimideHCID 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-dicyclohexylcarbodiimide (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-7fe910c2bc2c4d3385197ed225090611
Source dataset
uspto-grants-1997_02
Patent number
US05606028

Reaction notes

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