Serinol → HCID 21114417, compound

HRID 1866772Notes

Reaction equation

HRID 1866772 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][C:16](S(C)(=O)=O)=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:31].[NH2:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35]>CN1C(=O)CCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][C:16]([NH:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35])=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:31]

Participants

5

Reactant 2

HCID 68294SerinolHCID 10160942HCID 10160942, compound

Product 1

HCID 21114417HCID 21114417, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product of example 3 (90 mg, 0.2 mmol) was dissolved in NMP (1 mL) and serinol (91 mg, 1.0 mmol) was added. The solution was heated to 65° for 48 h, diluted with EtOAc (75 mL) and washed with 10% aq citric acid (2×), H2O, and satd aq NaCl, dried (Na2SO4), concentrated and purified by prep hplc to afford 46 mg (50%). LC MS m/z=460 (MH+), Rt=1.37 min

Workup

  1. temperatureThe solution was heated to 65° for 48 h
  2. washwashed with 10% aq citric acid (2×), H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by prep hplc
  6. customto afford 46 mg (50%)

Sources & evidence

ORD record
ord-b6f1a1e0b1b64f47bac29794469b8632
Source dataset
uspto-grants-2009_12
Patent number
US07629462B2

Reaction notes

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