Trifluoroacetic acid → (2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester

HRID 1353206Notes

Reaction equation

HRID 1353206 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C@@H:5]([O:22][CH3:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])=[CH:9][CH:8]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:24])[C@@H:5]([O:22][CH3:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58864672(2S)-3-(4-tert-butoxycarbonylmethoxy-phenyl)-2-methoxy-propionic acid ethyl ester

Product 1

HCID 58864673(2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of (2S)-3-(4-tert-butoxycarbonylmethoxy-phenyl)-2-methoxy-propionic acid ethyl ester (PREPARATION 3, step 1) (1.2 gr, 3.5 mmol) was solved in dichloromethane (5 ml) and trifluoroacetic acid was added (5 ml). The mixture was stirred for an hour, and the crude was concentrated to afford a yellow oil. 1H-NMR (CDCl3, 200.15 MHz): 7.16 (d, 2H, J=8.3), 6.75 (d, 2H, J=8.3), 4.89 (s, 2H), 4.14 (c, 2H, J=6.9), 3.94 (t, 1H, J=6.9), 3.57 (dc, 1H), 3.35 (dc, 1H), 2.92 (d, 2H, J=6.9), 1.23-1.10 (2t, 6H).

Workup

  1. concentrationthe crude was concentrated
  2. customto afford a yellow oil

Sources & evidence

ORD record
ord-222c882ec02b41f2b048d8883f0c32e5
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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