3-Ethyl-4-[(S)-2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid tert-butyl ester → (S)-3-Ethyl-4-[2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid

HRID 1958795Notes

Reaction equation

HRID 1958795 reaction equation
C([O:5][C:6](=[O:26])[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH2:15][C@@H:16]([OH:23])[CH2:17][NH:18][C:19](=[O:22])[CH2:20][OH:21])=[C:9]([CH2:24][CH3:25])[CH:8]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:24]([C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([CH3:13])[C:10]=1[O:14][CH2:15][C@@H:16]([OH:23])[CH2:17][NH:18][C:19](=[O:22])[CH2:20][OH:21])[C:6]([OH:26])=[O:5])[CH3:25]

Participants

4

Reactant 1

HCID 669319503-Ethyl-4-[(S)-2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid tert-butyl ester

Product 1

HCID 66931956(S)-3-Ethyl-4-[2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acidYield 43.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a cooled (0° C.) solution of 3-ethyl-4-[(S)-2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid tert-butyl ester (5.94 g, 16.2 mmol) in DCM (100 mL), TFA (5 mL) is added. The mixture is warmed to rt and stirred for 2 h. The mixture is concentrated, dissolved in acetonitrile/water (6 mL) and separated by prep. HPLC to give the title compound as a white powder (2.20 g). LC-MS: tR=0.41 min; [M+H]+=312.18.

Workup

  1. additionis added
  2. concentrationThe mixture is concentrated
  3. dissolutiondissolved in acetonitrile/water (6 mL)
  4. customseparated by prep

Sources & evidence

ORD record
ord-cc511b0a13384a7eb213e0b12537e7cd
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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