2-Mercaptoethanol → HCID 86743880, compound

HRID 1649711Notes

Reaction equation

HRID 1649711 reaction equation
[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH2:19][CH2:20][OH:21])(=[O:18])=[O:17])=[CH:12][C:11]=2[N+:22]([O-:24])=[O:23])[C:7](=[O:25])[C:6]=1[CH2:26]Cl)([CH3:4])([CH3:3])[CH3:2].[OH:28][CH2:29][CH2:30][SH:31].C(N(CC)CC)C>O1CCCC1>[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH2:19][CH2:20][OH:21])(=[O:18])=[O:17])=[CH:12][C:11]=2[N+:22]([O-:24])=[O:23])[C:7](=[O:25])[C:6]=1[CH2:26][S:31][CH2:30][CH2:29][OH:28])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 70374560HCID 70374560, compound

Product 1

HCID 86743880HCID 86743880, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15 g of 5-t-butyl-4-chloromethyl-2-(4-(2-hydroxyethylsulfonyl)-2-nitrophenyl)-4-iso-oxazolin-3-one was dissolved in 150 ml of tetrahydrofuran, 2.8 g of 2-hydroxyethanethiol and 4 g of triethylamine were added and the mixture was reacted at room temperature for a period of 5 hours. After reaction, the solvent was removed by distillation, ethyl acetate and water (150 ml:100 ml) were added and the mixture was partitioned. The organic layer was recovered, the solvent was removed by distillation and the residue obtained was used without further refinement in step 6.

Workup

  1. customthe mixture was reacted at room temperature for a period of 5 hours
  2. customAfter reaction
  3. customthe solvent was removed by distillation, ethyl acetate and water (150 ml:100 ml)
  4. additionwere added
  5. customthe mixture was partitioned
  6. customThe organic layer was recovered
  7. customthe solvent was removed by distillation
  8. customthe residue obtained

Sources & evidence

ORD record
ord-bcb196ca889d458598d893c4ecd58c03
Source dataset
uspto-grants-1990_05
Patent number
US04921785

Reaction notes

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