HCID 86649113, compound → HCID 86649112, compound

HRID 1411422Notes

Reaction equation

HRID 1411422 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[N:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][C:18]([C@:21]3([C:37](=[O:39])[NH2:38])[CH2:25][CH2:24][CH2:23][N:22]3[C:26](=[O:36])[C@@H:27]([NH:31][C:32](=[O:35])[O:33][CH3:34])[CH:28]([CH3:30])[CH3:29])=[C:17]([N+:40]([O-])=O)[CH:16]=2)[CH2:13][CH2:12][C@@H:11]1[C:43]1[CH:48]=[CH:47][C:46]([C@:49]2([C:65](=[O:67])[NH2:66])[CH2:53][CH2:52][CH2:51][N:50]2[C:54](=[O:64])[C@@H:55]([NH:59][C:60](=[O:63])[O:61][CH3:62])[CH:56]([CH3:58])[CH3:57])=[C:45]([N+:68]([O-])=O)[CH:44]=1>O1CCCC1.O.[Ni]>[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[N:10]1[C@@H:11]([C:43]2[CH:48]=[CH:47][C:46]([C@:49]3([C:65](=[O:67])[NH2:66])[CH2:53][CH2:52][CH2:51][N:50]3[C:54](=[O:64])[C@@H:55]([NH:59][C:60](=[O:63])[O:61][CH3:62])[CH:56]([CH3:58])[CH3:57])=[C:45]([NH2:68])[CH:44]=2)[CH2:12][CH2:13][C@@H:14]1[C:15]1[CH:20]=[CH:19][C:18]([C@:21]2([C:37](=[O:39])[NH2:38])[CH2:25][CH2:24][CH2:23][N:22]2[C:26](=[O:36])[C@@H:27]([NH:31][C:32](=[O:35])[O:33][CH3:34])[CH:28]([CH3:29])[CH3:30])=[C:17]([NH2:40])[CH:16]=1

Participants

5

Reactant 1

HCID 86649113HCID 86649113, compound

Product 1

HCID 86649112HCID 86649112, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl ([(2R,5R)-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)pyrrolidine-2,5-diyl]bis{(2-nitrobenzene-4,1-diyl)carbamoyl(2S)pyrrolidine-2,1-diyl[(2S)-3-methyl-1-oxobutane-1,2-diyl]})biscarbamate (ACD Name v12)) (0.59 g, 0.596 mmol) was dissolved in tetrahydrofuran (15 mL) and treated with Raney-nickel slurry in water (0.25 mL). The flask was evacuated and opened to a hydrogen balloon and stirred at ambient temperature for 1 hour. The solution was filtered through a silica plug and concentrated to dryness to give the title compound.

Workup

  1. customThe flask was evacuated
  2. filtrationThe solution was filtered through a silica plug
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6377470e1ac940798480ae00149710eb
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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