Trifluoroacetic acid → HCID 86727038, compound

HRID 2175793Notes

Reaction equation

HRID 2175793 reaction equation
[OH:1][C@@H:2]([C:19]1[C:20]([CH3:29])=[C:21]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[O:23][CH2:22]2)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12]C(C)(C)C)=[O:11])[CH2:6][C@H:5]1[CH2:17][OH:18].FC(F)(F)C(O)=O.C(N(CC)CC)C.ClC(O[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=O>C(Cl)Cl>[OH:1][C@@H:2]([C:19]1[C:20]([CH3:29])=[C:21]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[O:23][CH2:22]2)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:11])[CH2:6][C@H:5]1[CH2:17][OH:18]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 86727037(S)-tert-butyl 4-((S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Product 1

HCID 86727038HCID 86727038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 4-((S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate (2.57 g, 6.32 mmol) in methylene chloride (3 mL) was added trifluoroacetic acid (10 mL, 130 mmol) at rt for 1 h. After removing the volatiles under reduced pressure the residue was dissolved in methylene chloride (100 mL). To the above solution was added triethylamine (4.40 mL, 31.6 mmol) and benzyl chloroformate (0.95 mL, 6.64 mmol) at 0° C. for 0.5 h. The reaction was quenched by water followed by addition of saturated sodium carbonate. The mixture was extracted with methylene chloride, dried over sodium sulfate, concentrated and the residue was purified by MPLC on a Biotage system using 40-100% EtOAc/hexane to give the title compound. LC/MS: (M+1)+: 441.11.

Workup

  1. customAfter removing the volatiles under reduced pressure the residue
  2. dissolutionwas dissolved in methylene chloride (100 mL)
  3. customThe reaction was quenched by water
  4. additionfollowed by addition of saturated sodium carbonate
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customthe residue was purified by MPLC on a Biotage system

Sources & evidence

ORD record
ord-750fc3af2fa44ba3bbe0570a244af988
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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