Ethyl Thioglycolate → HCID 118036756, compound

HRID 1778012Notes

Reaction equation

HRID 1778012 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].CC1C=CC(S(O[CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])(=O)=O)=CC=1>C1COCC1.C(OCC)(=O)C.O>[C:27]([O:26][C:24]([NH:23][CH2:22][CH2:21][S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 10781634tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate2×

Product 1

HCID 118036756HCID 118036756, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-mercaptoacetate (0.593 mL, 5.25 mmol) in THF (10 ml) was added to a suspension of NaH (60% dispersion in mineral oil, 204 mg, 5.10 mmol) in THF (20 ml) at room temperature, followed by the addition of a solution of 2-((tert-butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate (intermediate 212, 1.71 g, 4.61 mmol) in THF (20 ml). The reaction mixture was stirred at room temperature for approximately 20 h and diluted with ethyl acetate and water. Layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried using MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography eluting with a gradient of EtOAc (0-40%) in hexane. Fractions containing the product were combined and evaporated to yield the title compound as colorless oil. (UPLC-MS 3) ESI-MS 264.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 4.93 (br s, 1H), 4.25-4.14 (m, 2H), 3.39-3.30 (m, 2H), 3.23 (s, 2H), 2.77 (t, 2H), 1.44 (s, 9H), 1.35-1.21 (t, 3H).

Workup

  1. customLayers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography
  8. washeluting with a gradient of EtOAc (0-40%) in hexane
  9. additionFractions containing the product
  10. customevaporated

Sources & evidence

ORD record
ord-c7c7afee809b41c2ac7e2e16806355b7
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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