HCID 57320168, compound → HCID 57057802, compound

HRID 1439976Notes

Reaction equation

HRID 1439976 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([NH:10][C:11](=[O:30])[C@H:12]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:8][CH2:7][O:6]1)(=[O:3])[CH3:2]>C(O)C>[C:1]([O:4][C@H:5]1[C@@H:9]([NH:10][C:11](=[O:30])[C@H:12]([CH2:26][CH:27]([CH3:28])[CH3:29])[NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH2:8][CH2:7][O:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 57320168HCID 57320168, compound

Product 1

HCID 57057802HCID 57057802, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (100 ml) was dissolved (2S,3S)-2-acetoxy-3-[[N-(4-nitrobenzenesulfonyl)-(L)-leucyl]amino]tetrahydrofuran (1.0 g) followed by addition of palladum-on-carbon (5%, 0.5 g) and the catalytic hydrogenation was carried out at ambient temperature and atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to provide (2S,3S)-2-acetoxy-3-[[N-(4-aminobenzenesulfonyl)-(L)-leucyl]amino]tetrahydrofuran (chemical formula below) (0.7 g, 74%). As recrystallized from ethyl acetate-methonol-ether, colorless needles, m.p. 189°-190° C., optical rotation [α]D -59.2° (C=0.27, dimethyl sulfoxide) ##STR69##

Workup

  1. customwas carried out at ambient temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3d96f1cc681f439c964edac873abf0b8
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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