Trifluoroacetic acid → HCID 131727396, compound

HRID 2109852Notes

Reaction equation

HRID 2109852 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13](=[O:33])[C:14]([CH2:19][CH:20]4[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]4)=[C:15]([OH:18])[C:16]([OH:17])=[C:9]3[C:8]2=[O:34])=[CH:4][CH:3]=1.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl>[OH:41][C:39]([C:38]([F:43])([F:42])[F:37])=[O:40].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13](=[O:33])[C:14]([CH2:19][CH:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)=[C:15]([OH:18])[C:16]([OH:17])=[C:9]3[C:8]2=[O:34])=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57634650HCID 57634650, compound

Product 1

HCID 131727396HCID 131727396, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of tert-butyl 4-{[2-(4-fluorobenzyl)-8,9-dihydroxy-1,6-dioxo-1,3,4,6-tetrahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methyl}piperidine-1-carboxylate (1.12 g, 2.23 mmol) in methylene chloride (10 mL), trifluoroacetic acid (3.4 mL, 45 mmol) was added and the mixture was stirred for 2 hours. The mixture was concentrated in vacuo and the residue was purified by prep HPLC (Waters prep LC 4000 System using a Waters Nova Pak column [3*10×40 mm I.D. cartridges, C18, 6 μM pore size) eluting with 95-5% water (0.10% TFA)/acetonitrile (0.10% TFA) gradient at 60 mL/min]. Combined and concentrated the product fractions to give a yellow solid. The solids were triturated with acetonitrile and collected by vacuum filtration.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by prep HPLC (Waters prep LC 4000 System
  3. washcartridges, C18, 6 μM pore size) eluting with 95-5% water (0.10% TFA)/acetonitrile (0.10% TFA) gradient at 60 mL/min]
  4. concentrationconcentrated the product fractions
  5. customto give a yellow solid
  6. customThe solids were triturated with acetonitrile
  7. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-f38777628fb745c6bc36ebe88dbc492e
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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