HCID 86594120, compound → HCID 69584869, compound

HRID 2212454Notes

Reaction equation

HRID 2212454 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@@:10]([NH:23][NH:24]C(OC(C)(C)C)=O)([CH3:22])[C:11]([O:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]>ClCCl.FC(F)(F)C(O)=O>[C:15]([CH2:14][O:13][C:11](=[O:12])[C@:10]([NH:23][NH2:24])([CH3:22])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)([OH:17])=[O:16]

Participants

4

Reactant 1

HCID 86594120HCID 86594120, compound

Product 1

HCID 69584869HCID 69584869, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound 230 (441 mg, 1 mmol) in 1:1 (v/v) dichloromethane and trifluoroacetic acid was stirred at room temperature for 8 h (monitored by LC/MS). After removing the solvent under reduced pressure at room temperature, the residue was purified by preparative LC/MS technique to afford 165 mg (58%) of the title compound as a light yellow solid. 1H NMR (400 MHz, CD3OD): δ1.39 (3H, s), 2.93 (2H, m), 4.56 (1H, d), 4.75 (1H, d), 6.50 (1H, dd), 6.60 (1H, d), 6.67 (1H, d). MS (ESI) m/z 285.26 (M+H+) and 283.13 (M−H−).

Workup

  1. customAfter removing the solvent under reduced pressure at room temperature
  2. customthe residue was purified by preparative LC/MS technique

Sources & evidence

ORD record
ord-31740b164b574361812be0ee974b16ad
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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