Acetic Anhydride → HCID 14583105, compound

HRID 868317Notes

Reaction equation

HRID 868317 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([C:10]1[C:11](=[O:49])[N:12]2[C:16](=[CH:17][C:18]=1[C@:19]([CH2:43][CH3:44])([O:25][C:26]([C@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[S:33]([C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=1)(=[O:35])=[O:34])=[O:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]1([O:48][CH2:47][CH2:46][O:45]1)[CH2:14][CH2:13]2)#[N:9]>[Ni].C(O)(=O)C>[C:1]([NH:9][CH2:8][C:10]1[C:11](=[O:49])[N:12]2[C:16](=[CH:17][C:18]=1[C@:19]([CH2:43][CH3:44])([O:25][C:26]([C@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[S:33]([C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=1)(=[O:34])=[O:35])=[O:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]1([O:45][CH2:46][CH2:47][O:48]1)[CH2:14][CH2:13]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 14306189HCID 14306189, compound2×

Product 1

HCID 14583105HCID 14583105, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixed solvent which was composed of 20 ml of acetic acid and 50 ml of acetic anhydride and containing 6 g of Raney nickel, 2.00 g of the compound (XIII) obtained in the above procedure (3) was added. While exposing the reaction system to light from a tungsten lamp, the compound (XIII) was reduced for 2 hours under a hydrogen gas stream. After removal of Raney nickel by filtration, the filtrate was concentrated. The residue was subjected to column chromatography on silica gel and then developed by a 50:1 mixed solvent of chloroform and methanol. A fraction containing the intended product was concentrated to drynes,s thereby obtaining 2.15 g of the title compound in an amorphous form.

Workup

  1. customobtained in the above procedure (3)
  2. additionwas added
  3. customAfter removal of Raney nickel
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated
  6. additionA fraction containing the intended product
  7. concentrationwas concentrated to drynes,s

Sources & evidence

ORD record
ord-6670aabf6a4042f29f0a22323710d860
Source dataset
uspto-grants-1988_10
Patent number
US04778891

Reaction notes

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