HCID 163786, compound → HCID 197389, compound

HRID 393862Notes

Reaction equation

HRID 393862 reaction equation
[CH3:1][CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][CH:18]1[C:49](=[O:50])[NH:48][CH:47]([CH:51]([OH:53])[CH3:52])[C:45](=[O:46])[N:44]2[CH:40]([CH2:41][CH:42]([OH:54])[CH2:43]2)[C:38](=[O:39])[NH:37][CH:36]([CH:55]([OH:65])[CH:56](O)[C:57]2[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=2)[C:34](=[O:35])[NH:33][CH:32]([CH2:66][OH:67])[C:30](=[O:31])[N:29]2[CH:25]([CH:26]([OH:69])[CH:27]([CH3:68])[CH2:28]2)[C:23](=[O:24])[NH:22][CH:21]([OH:70])[CH:20]([OH:71])[CH2:19]1)=[O:16])[CH3:4]>C(O)C.[Ni]>[CH3:1][CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][CH:18]1[C:49](=[O:50])[NH:48][CH:47]([CH:51]([OH:53])[CH3:52])[C:45](=[O:46])[N:44]2[CH:40]([CH2:41][CH:42]([OH:54])[CH2:43]2)[C:38](=[O:39])[NH:37][CH:36]([CH:55]([OH:65])[CH2:56][C:57]2[CH:62]=[CH:61][C:60]([OH:63])=[CH:59][CH:58]=2)[C:34](=[O:35])[NH:33][CH:32]([CH2:66][OH:67])[C:30](=[O:31])[N:29]2[CH:25]([CH:26]([OH:69])[CH:27]([CH3:68])[CH2:28]2)[C:23](=[O:24])[NH:22][CH:21]([OH:70])[CH:20]([OH:71])[CH2:19]1)=[O:16])[CH3:4]

Participants

4

Reactant 1

HCID 163786HCID 163786, compound

Product 1

HCID 197389HCID 197389, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

Mulundocandin (220 mg, 2.2 mM) in ethanol (8 ml)) was stirred with 15 ml of W-2 Raney nickel (pH 7) in ethanol (30 ml) for 3 hours at room temperature. After standing for 15 minutes the supernatent solution was decanted and Raney nickel washed with 3×30 ml. ethanol with stirring and filtered. Combined ethanolic solutions were concentrated by distillation under a reduced pressure of 60-70 mm/Hg at 35° C. to obtain 160 mg (75%) of crude deoxymulundocandin as a slightly green solid.

Workup

  1. customthe supernatent solution was decanted
  2. washRaney nickel washed with 3×30 ml
  3. filtrationfiltered
  4. concentrationCombined ethanolic solutions were concentrated by distillation under a reduced pressure of 60-70 mm/Hg at 35° C.

Sources & evidence

ORD record
ord-0fb7690acb2a48d89f6811c3fb52c95d
Source dataset
uspto-grants-2004_10
Patent number
US06809177B1

Reaction notes

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