HCID 58646553, compound → HCID 58646561, compound

HRID 1353264Notes

Reaction equation

HRID 1353264 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C@@H:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C@H:14]([C:16]([O:18]C(C)(C)C)=[O:17])[CH3:15])=[CH:9][CH:8]=1)[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O.O>[CH2:1]([O:3][C:4](=[O:26])[C@@H:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C@H:14]([C:16]([OH:18])=[O:17])[CH3:15])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 1

HCID 58646553HCID 58646553, compound

Product 1

HCID 58646561HCID 58646561, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S,S)-3-[4-(1-tert-butoxycarbonyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester (1.10 g, 3.00 mmol) in CH2Cl2 (5.0 ml) and TFA (4.0 ml) and water (0.2 ml) was stirred for 12 hours. The mixture was concentrated to a residue and purified by silica gel chromatography with EtOAc/Hexanes (50%) to afford the acid product (0.91 g, 98%).

Workup

  1. concentrationThe mixture was concentrated to a residue
  2. custompurified by silica gel chromatography with EtOAc/Hexanes (50%)

Sources & evidence

ORD record
ord-4168b41fa76f4467a32f3c8d8a111cb9
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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