methyl (2S,3R,5E)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-ethoxy-6-(3-fluoro-4-phenoxyphenyl)hex-5-enoate → methyl (2S,3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-ethoxy-6-(3-fluoro-4-phenoxyphenyl)hexanoate

HRID 1700982Notes

Reaction equation

HRID 1700982 reaction equation
[CH3:1][C:2]([CH3:45])([CH3:44])[C@H:3]([NH:15][C:16]([C@H:18]([CH2:27]/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:32]([F:43])[CH:31]=1)[C@H:19]([O:24][CH2:25][CH3:26])[C:20]([O:22][CH3:23])=[O:21])=[O:17])[C:4]([NH:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:5]>C(O)C.[Pd]>[CH3:45][C:2]([CH3:1])([CH3:44])[C@H:3]([NH:15][C:16]([C@H:18]([CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[C:32]([F:43])[CH:31]=1)[C@H:19]([O:24][CH2:25][CH3:26])[C:20]([O:22][CH3:23])=[O:21])=[O:17])[C:4]([NH:6][C@@H:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 86757821methyl (2S,3R,5E)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-ethoxy-6-(3-fluoro-4-phenoxyphenyl)hex-5-enoate

Product 1

HCID 57064299methyl (2S,3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-ethoxy-6-(3-fluoro-4-phenoxyphenyl)hexanoateYield 104,740.398%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl (2S,3R,5E)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-ethoxy-6-(3-fluoro-4-phenoxyphenyl)hex-5-enoate (350 mg, 0.566 mmol) in ethanol (15 mL) was hydrogenated over 10% palladium on charcoal (60 mg) at 3 bar and 20° C. for 16 h. The mixture was filtered through Arbocel filter aid and concentrated under reduced pressure. The residue was dissolved in cyclohexane and evaporated (twice) to give methyl (2S,3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-2-ethoxy-6-(3-fluoro-4-phenoxyphenyl)hexanoate (368 gm, 105%), as a colourless foam, which was taken onto the next step without purification.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in cyclohexane
  5. customevaporated (twice)

Sources & evidence

ORD record
ord-5eea9ae05e904cfda810156add416242
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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