Trifluoroacetic acid → HCID 178525680, compound

HRID 278201Notes

Reaction equation

HRID 278201 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[CH2:8]([C:15]1[CH:19]=[C:18]([CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[NH:17][N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(OC)C=CC=CC=1.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>C(Cl)Cl>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[OH:47][C:41]([C:43]([F:46])([F:45])[F:44])=[O:42].[CH2:8]([C:15]1[CH:19]=[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[NH:17][N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178451738HCID 178451738, compound

Product 1

HCID 178525680HCID 178525680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-benzyl-(1H-pyrazol-5-yl))-1-(t-butoxycarbonyl)piperidine TFA salt (from Step A) in methylene chloride (1.5 mL) was added anisole (0.017 mL) and TFA (0.230 mL). After several h at rt, volatiles were removed under reduced pressure. Purification of the residue was done by preparative reverse-phase HPLC using a 9.4×250 mm Semi-preparative Zorbax SB-C18 column with a 15-25% acetonitrile gradient in water having 0.5% (v/v) TFA over 15 min at 6.0 mL per minute to give the title compound (40.7 mg) as a gel.

Workup

  1. customAfter several h at rt, volatiles were removed under reduced pressure
  2. customPurification of the residue
  3. customover 15 min

Sources & evidence

ORD record
ord-ea3fc7eda6cb4208a6840f3123ee43e0
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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