Sodium Thiosulfate → HCID 86588567, compound

HRID 1368883Notes

Reaction equation

HRID 1368883 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([O:27][P:28]([CH:38]([NH:42]CC1C=CC(OC)=CC=1)[CH:39]([CH3:41])[CH3:40])([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+].[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[NH2:42][CH:38]([P:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([O:27][C@@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:29])[CH:39]([CH3:41])[CH3:40]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 180504Ceric ammonium nitrateHCID 131723921HCID 131723921, compound

Product 1

HCID 86588567HCID 86588567, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

The crude benzyl (S)-6-benzyloxycarbonylamino-2-((1-((4-methoxy)benzylamino)-2-methylpropyl)(benzyloxyphosphinoyl)oxy)hexanoate (557.4 mg) obtained in the above step (d) was dissolved in a mixed solvent of acetonitrile and water (4:1) (5.6 ml). Cerium(IV) diammonium nitrate was dissolved in a mixed solvent of acetonitrile and water (4:1) (5.6 ml), and the resulting solution was added to the reaction system. The mixture was stirred at room temperature for 1.5 hours. The mixture was cooled to 0° C. and added with saturated aqueous sodium thiosulfate, and further stirred at room temperature for 30 minutes. The organic substances were extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure, and then the residue was roughly purified by silica gel column chromatography (25 g, hexane:ethyl acetate:acetic acid=250:50:1.5 to chloroform:methanol=30:1) to obtain crude benzyl (S)-2-((1-amino-2-methylpropyl)(benzyloxyphosphinoyl)oxy)-6-benzyloxycarbonylaminohexanoate (271 mg, 62%). This compound was examined in the molecular weight and then used in the following reaction without further purification.

Workup

  1. additionthe resulting solution was added to the reaction system
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringfurther stirred at room temperature for 30 minutes
  4. extractionThe organic substances were extracted with ethyl acetate
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customthe residue was roughly purified by silica gel column chromatography (25 g, hexane:ethyl acetate:acetic acid=250:50:1.5 to chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-80f22f2019564aa891cb91edee485e5f
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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