RO5068760 → HCID 57935194, compound

HRID 1433763Notes

Reaction equation

HRID 1433763 reaction equation
[OH:1][C@H:2]([CH2:38][OH:39])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[C:15](=[O:16])[N:14]([C@@H:17]([C@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:30])[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[O:19])[C:13](=[O:37])[NH:12]2)=[CH:7][CH:6]=1>CO>[OH:1][C@H:2]([CH2:38][OH:39])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[C:15](=[O:16])[N:14]([C@@H:17]([C@H:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH3:30])[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[O:19])[C:13](=[O:37])[NH:12]2)=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 17757766RO5068760

Product 1

HCID 57935194HCID 57935194, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,3S)-2-{(R)-4-[4-((R)-2,3-Dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide (prepared as described in example 56) (160 mg, 0.25 mmol) was dissolved in methanol (10 ml) and allowed to stir for 48 hours at ambient temperature followed by warming to 50° C. for an additional 6 hours. The solvent was removed in vacuo and the residue was then purified by super-critical fluid chromatography using a Chiracel OD column eluted with carbon dioxide at 100 bar and 30° C. containing 35% methanol in acetonitrile eluted at 2 mL/minute. The second eluted compound was collected and concentrated in vacuo to obtain (2S,3S)-2-{(S)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide as a colorless solid (35 mg, 44%). The compound eluted first was identical with (2S,3S)-2-{(R)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide.

Workup

  1. temperatureby warming to 50° C. for an additional 6 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was then purified by super-critical fluid chromatography
  4. washeluted with carbon dioxide at 100 bar and 30° C.
  5. additioncontaining 35% methanol in acetonitrile
  6. washeluted at 2 mL/minute
  7. customThe second eluted compound was collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79ebbf3a4a514f0fa31ae5d13b9c67bc
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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