Trifluoroacetic acid → HCID 71060581, compound

HRID 1036689Notes

Reaction equation

HRID 1036689 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[C:9]([N:11]1[CH2:28][CH2:27][CH2:26][C:13]2([C:17](=[O:18])[N:16]([CH3:19])[CH2:15][CH:14]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@H:8]([CH2:29][O:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=1)[C:9]([N:11]1[CH2:28][CH2:27][CH2:26][C:13]2([C:17](=[O:18])[N:16]([CH3:19])[CH2:15][CH:14]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:12]1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060603HCID 71060603, compound

Product 1

HCID 71060581HCID 71060581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of [(R)-1-(4-Fluoro-benzyloxymethyl)-2-(2-methyl-1-oxo-4-phenyl-2,7-diaza-spiro[4.5]dec-7-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (diastereomer 2 from step 1) (185 mg, 0.34 mmol) in DCM (4 ml) was treated with TFA (0.79 ml, 10.3 mmol). The resulting solution was stirred for 2 h at RT. The reaction mixture was diluted with DCM (20 ml) and quenched at 0° C. with 2M NaOH aqueous solution (10 ml). The organic phase was separated, washed with brine (5 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound.

Workup

  1. customquenched at 0° C. with 2M NaOH aqueous solution (10 ml)
  2. customThe organic phase was separated
  3. washwashed with brine (5 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84699306e13d4e069ff137fa8b6a7754
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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