benzyl (3R)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate → Benzyl(3R)-1-((2S)-2-{(3S)-3-[(2-naphthylsulfonyl)amino]-2-oxopyrrolidin-1-yl}propanoyl)piperidin-3-ylcarbamate

HRID 7321Notes

Reaction equation

HRID 7321 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:41])[C:22]([N:24]3[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:25]3)=[O:23])[C:17]1=[O:42])(=[O:14])=[O:13])[CH:6]=[CH:5]2>[Pd].C(O)C>[CH:8]1[C:9]2[C:4](=[CH:3][CH:2]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:41])[C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:25]2)=[O:23])[C:17]1=[O:42])(=[O:13])=[O:14]

Participants

4

Reactant 1

HCID 86593865benzyl (3R)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate

Product 1

HCID 86593864Benzyl(3R)-1-((2S)-2-{(3S)-3-[(2-naphthylsulfonyl)amino]-2-oxopyrrolidin-1-yl}propanoyl)piperidin-3-ylcarbamateYield 3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl (3R)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate (0.350 g), 10% palladium on carbon (0.035 g) and ethanol (1000 ml) was stirred under an atmosphere of hydrogen for 17 h. The reaction mixture was filtered through Harbolite™ and the filtrate was concentrated under reduced pressure to give an oil. The oil was partially purified using SPE (silica, eluting with methanol and then 10% aqueous ammonia in methanol) and then fully purified using mass directed preparative h.p.l.c. to give the title compounds (Example 403, 0.01 g; Example 404, 0.028 g), both as oils.

Workup

  1. filtrationThe reaction mixture was filtered through Harbolite™
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give an oil
  4. customThe oil was partially purified
  5. washeluting with methanol
  6. custom10% aqueous ammonia in methanol) and then fully purified

Sources & evidence

ORD record
ord-89d649d4b7be4c728ab42cad047e2397
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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