HCID 66942061, compound → HCID 68674419, compound

HRID 643126Notes

Reaction equation

HRID 643126 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C:17](=[O:21])[C:18]([OH:20])=[O:19])=[CH:11][C:10]=1[Cl:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][C@@H:17]([OH:21])[C:18]([OH:20])=[O:19])=[CH:11][C:10]=1[Cl:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66942061HCID 66942061, compound

Product 1

HCID 68674419HCID 68674419, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(R)-3-(4-benzyloxy-3-chloro-5-methyl-phenyl)-2-hydroxy-propionic acid was prepared analogously to Example 7d from 15.5 g (48.6 mmol) 3-(4-benzyloxy-3-chloro-5-methyl-phenyl)-2-oxo-propionic acid and 27.6 g (86.1 mmol) (1R)-B-chlorodiisopinocampheylborane. The crude product was combined with 150 mL methanolic HCl (1.25 M) and stirred overnight at RT. The reaction solution was evaporated down i.vac., the residue was combined with 70 mL 15% K2CO3 solution and extracted twice with 50 mL EtOAc. The combined organic extracts were dried, filtered and evaporated down i.vac.

Workup

  1. customThe reaction solution was evaporated down i.vac
  2. extractionextracted twice with 50 mL EtOAc
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. customevaporated down i.vac

Sources & evidence

ORD record
ord-380d9efc6b404b7b9a1c29304c28812e
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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