Acetic Acid → HCID 69237821, compound

HRID 221189Notes

Reaction equation

HRID 221189 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C:10](=[O:11])[CH:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][S:7]1)=[O:5])[CH3:2].[BH4-].[Na+].CC(C)=O.C(O)(=O)C>CCO>[CH2:1]([O:3][C:4]([C@H:6]1[CH:10]([OH:11])[CH:9]([NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:8][S:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 4311764Sodium borohydrideHCID 69238679HCID 69238679, compound

Product 1

HCID 69237821HCID 69237821, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

reduction: The oxo-ester (13) (9.16 g, 31.7 mmole) in EtOH 90 mL was reduced with NaBH4 (844 mg, 22 mmole) added portion wise at −30° C. After 30 min at −30° C., acetone 8.7 mL followed with acetic acid 1.1 mL were added. The crude mixture was concentrated at 40° C. under 100 mbar, extracted with EtOAc and brine to pH 7. The solvent was removed under 0.1 mbar, crude 9.20 g (yield 99%) of (R)-ethyl-4-[(tert-butoxycarbonyl)amino]tetrahydro-3-hydroxy-2-thiophenecarboxylate.

Workup

  1. additionadded portion wise at −30° C
  2. additionwere added
  3. concentrationThe crude mixture was concentrated at 40° C. under 100 mbar
  4. extractionextracted with EtOAc and brine to pH 7
  5. customThe solvent was removed under 0.1 mbar

Sources & evidence

ORD record
ord-32b39be7831a44c0b2c523651223e703
Source dataset
uspto-grants-2012_06
Patent number
US08206692B2

Reaction notes

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