HCID 66942061, compound → HCID 68674419, compound

HRID 491137Notes

Reaction equation

HRID 491137 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-fd7f514f8b134ee79c491937b93d52f4
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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