Hydrochloric Acid → HCID 9992969, compound

HRID 1440814Notes

Reaction equation

HRID 1440814 reaction equation
C[O-].[Na+].O.Cl.[OH:6][C:7]1[C:8]([CH3:24])=[C:9]([CH3:23])[C:10]2[O:15][C@:14]([CH3:20])([CH2:16][C:17]([OH:19])=[O:18])[CH2:13][CH2:12][C:11]=2[C:21]=1[CH3:22]>CO>[OH:6][C:7]1[C:8]([CH3:24])=[C:9]([CH3:23])[C:10]2[O:15][C@@:14]([CH3:20])([CH2:16][C:17]([OH:19])=[O:18])[CH2:13][CH2:12][C:11]=2[C:21]=1[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 11021753HCID 11021753, compound

Product 1

HCID 9992969HCID 9992969, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

This crude enriched (R)-ester (1.1 g) was dissolved in MeOH (8 mL) and treated with NaOMe (2.7 mL of a 25 wt % solution in MeOH, 12 mmol). This solution was heated at reflux for 24 h when H2O (2 mL) was added to the hot solution and reflux was maintained for an additional 30 min. The solution was cooled to room temperature, 1M HCl (15 mL) was added, and the mixture was stirred vigorously for 1 h. The solid was isolated by filtration, washed with H2O (2×5 mL), and air-dried overnight to give 0.70 g (70% yield; essentially 1:1/(R):(S), Method A) of (R,S)-acid of Formula (XI) as a brown solid.

Workup

  1. temperatureThis solution was heated
  2. additionwas added to the hot solution
  3. temperaturereflux
  4. temperaturewas maintained for an additional 30 min
  5. customThe solid was isolated by filtration
  6. washwashed with H2O (2×5 mL)
  7. customair-dried overnight
  8. customto give 0.70 g (70% yield

Sources & evidence

ORD record
ord-7fb91f882bd543769efedb7a7759132c
Source dataset
uspto-grants-1996_03
Patent number
US05500444

Reaction notes

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