HCID 67442531, compound → HCID 67448275, compound

HRID 1400803Notes

Reaction equation

HRID 1400803 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][CH:37]([CH:42](C(O)=O)[C:43]([OH:45])=[O:44])[C:38]([F:41])([F:40])[F:39])=[CH:32][C:31]=3[F:49])[CH:21]=2)=[N:18][CH:19]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][CH:37]([C:38]([F:40])([F:39])[F:41])[CH2:42][C:43]([OH:45])=[O:44])=[CH:32][C:31]=3[F:49])[CH:21]=2)=[N:18][CH:19]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 67442531HCID 67442531, compound

Product 1

HCID 67448275HCID 67448275, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 17 (1.21 g, mixture of 17 and 18) in toluene (50 mL) was heated to reflux for 1 h then cooled to RT. The reaction mixture was then concentrated, re-dissolved in MeOH, and concentrated again. The residue was triturated with a mixture of AcOEt/hexanes. The resulting suspension (gel) was collected by filtration, rinsed with hexanes, air-dried and dried under high vacuum to afford the title compound 18 (1.157 g, 1.74 mmol, quant, yield) as an off-white solid. MS (m/z): 665.6 (M+H).

Workup

  1. temperatureto reflux for 1 h
  2. concentrationThe reaction mixture was then concentrated
  3. dissolutionre-dissolved in MeOH
  4. concentrationconcentrated again
  5. customThe residue was triturated with a mixture of AcOEt/hexanes
  6. filtrationThe resulting suspension (gel) was collected by filtration
  7. washrinsed with hexanes
  8. customair-dried
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-988c44099df544b5b55828f5f80757d3
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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