HCID 17757765, compound → HCID 57935198, compound

HRID 1433760Notes

Reaction equation

HRID 1433760 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:37])[C@@H:11]([N:20]1[C:24](=[O:25])[C@@H:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][OH:35])=[CH:28][CH:27]=2)[NH:22][C:21]1=[O:36])[C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13]>CO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:37])[C@@H:11]([N:20]1[C:24](=[O:25])[C@H:23]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][OH:35])=[CH:30][CH:31]=2)[NH:22][C:21]1=[O:36])[C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13]

Participants

3

Reactant 1

HCID 17757765HCID 17757765, compound

Product 1

HCID 57935198HCID 57935198, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S,3S)—N-(2-fluoro-4-iodo-phenyl)-2-{(R)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (prepared as described in example 48) (50 mg, 0.081 mmol) was dissolved in methanol (3 mL) and stirred at ambient temperature for 4 days. The resulting mixture of isomers was concentrated in vacuo and then purified by super-critical fluid chromatography using a Chiracel OJ column eluted with carbon dioxide at 100 bar and 30° C. modified with 35% v/v ethanol in acetonitrile eluted at 2 mL/minute. The first eluted compound was collected and concentrated in vacuo to obtain (2S,3S)—N-(2-fluoro-4-iodo-phenyl)-2-{(S)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (9.1 mg, 18%) The compound eluted second was identical with (2S,3S)—N-(2-fluoro-4-iodo-phenyl)-2-{(R)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (19.9 mg, 40%).

Workup

  1. additionThe resulting mixture of isomers
  2. concentrationwas concentrated in vacuo
  3. custompurified by super-critical fluid chromatography
  4. washeluted with carbon dioxide at 100 bar and 30° C.
  5. washeluted at 2 mL/minute
  6. customThe first eluted compound was collected
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-899649d9a49142b896f357cc7cdeb375
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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