2-Mercaptoethanol → HCID 14958432, compound

HRID 523617Notes

Reaction equation

HRID 523617 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(N(CC)CC)C.[SH:17][CH2:18][CH2:19][OH:20].C(OC(=O)C)C>C(Cl)Cl.CCCCCC>[OH:20][CH2:19][CH2:18][S:17][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 14958432HCID 14958432, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

tert-butyl bromoacetate 1 (15 g, 0.077 mol, 1 eqv.) and triethylamine (16 g, 0.16 mol, 2 eqv.) were dissolved in CH2Cl2 (100 mL) under nitrogen and cooled to 0 C. 2-mercaptoethanol (6.3 g, 0.081 mol, 1.05 eqv.) was slowly added to the mixture and the reaction mixture was warmed to room temperature. The reaction was stirred for 1 additional hour. Completion of the reaction was monitored by TLC (ethylacetate (EtOAc):hexane (Hex), 1:1 (v/v), Rf: 0.88). Base and acid extractions were carried out with 1M KCO3, pH 10 and 1M NaOAc pH 3.5, twice, respectively. The combined organic layers were washed with brine, dried with MgSO4 and filtered through Ø 185 mm whatman filter papers. The filtrate was concentrated in vacuo (CH2Cl2) to obtain 9.2 g (62% yield) 2 as a colourless oil.

Workup

  1. temperaturecooled to 0 C
  2. extractionBase and acid extractions
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered through Ø 185 mm whatman
  6. filtrationfilter papers
  7. concentrationThe filtrate was concentrated in vacuo (CH2Cl2)

Sources & evidence

ORD record
ord-1ee31a36152c489b87b84ad74ad4a265
Source dataset
uspto-grants-2016_05
Patent number
US09339554B2

Reaction notes

Loading…