Citric Acid → HCID 58573626, compound

HRID 931946Notes

Reaction equation

HRID 931946 reaction equation
[CH2:1]([C@@H:4]1[C:9](=[O:10])[N:8]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[C@:7]2([C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[N:16]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:15]2=[O:32])[C@@H:6]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=2)[CH2:5]1)[CH:2]=C.I([O-])(=O)(=O)=[O:41].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[OH2:59].C(Cl)(Cl)(Cl)Cl.CC#N>O.[Ru](Cl)(Cl)Cl>[Cl:23][C:19]1[CH:18]=[C:17]2[N:16]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:31])[CH3:29])[C:15](=[O:32])[C@:7]3([C@@H:6]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=4)[CH2:5][C@H:4]([CH2:1][C:2]([OH:41])=[O:59])[C:9](=[O:10])[N:8]3[CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:22]2=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 22592919water acetonitrile CCl4HCID 23667635Sodium periodateHCID 58573467HCID 58573467, compound

Product 1

HCID 58573626HCID 58573626, compound

Reagents, catalysts & solvents 1

HCID 6093376Ruthenium trichloride hydrateCatalyst

Procedure

To a rapidly stirred solution of (rac) (2′S,3′R,5′S)-5′-allyl-6-chloro-3′-(3-chlorophenyl)-1′-(cyclopropylmethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)spiro[indoline-3,2′-piperidine]-2,6′-dione (Example 62, Step J) (46 mg, 0.079 mmol) in H2O/CCl4/MeCN (0.75 ml/0.5 mL/0.5 mL) was added sodium periodate (67.2 mg, 0.314 mmol) and ruthenium(III) chloride hydrate (1.771 mg, 7.85 μmol). The reaction mixture was stirred vigorously for 19 h and then acidified (10% citric acid) and filtered through a plug of celite and washed with EtOAc. The filtrate was transferred to a separatory funnel and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide the title compound.

Workup

  1. filtrationfiltered through a plug of celite
  2. washwashed with EtOAc
  3. customThe filtrate was transferred to a separatory funnel
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-beba4714f7cf4b518be168f977767f7c
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

Loading…