Water → Water TFA acetonitrile

HRID 2273056Notes

Reaction equation

HRID 2273056 reaction equation
[CH2:1]([O:4][C@H:5]1[C@H:9]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH2:19])[O:8][C@H:7]([CH2:20][C@@H:21]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:22][CH2:23][C@H:24]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:25]([OH:27])=[O:26])[C@H:6]1[OH:44])[CH:2]=C.[O:45]1CCCC1.I([O-])(=O)(=O)=[O:51].[Na+].[C:56](#[N:58])[CH3:57].O.[C:60]([OH:66])([C:62]([F:65])([F:64])[F:63])=[O:61].O>O.O.[Os](=O)(=O)(=O)=O.[K]>[NH2:19][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[C:16]=1[N:17]=[CH:18][N:10]2[C@@H:9]1[O:8][C@H:7]([CH2:20][C@@H:21]([NH:36][C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH2:22][CH2:23][C@H:24]([NH:28][C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C:25]([OH:27])=[O:26])[C@@H:6]([OH:44])[C@H:5]1[O:4][CH2:1][CH:2]=[O:45].[C:56](#[N:58])[CH3:57].[OH2:51].[C:60]([OH:66])([C:62]([F:65])([F:64])[F:63])=[O:61]

Participants

8

Reactant 5

HCID 962Water2×HCID 8028TetrahydrofuranHCID 22145617Water TFA acetonitrileHCID 23667635Sodium periodateHCID 86673680HCID 86673680, compound

Product 2

HCID 22145617Water TFA acetonitrileHCID 86673679HCID 86673679, compound

Reagents, catalysts & solvents 1

HCID 131733378HCID 131733378, compoundCatalyst

Procedure

To a 7-mL scintillation vial containing Compound 10 (2.0 mg, 0.0032 mmol) was added sequentially tetrahydrofuran (200 μL), water (132 μL), sodium periodate (3.3 mg, 0.015 mmol), and a mixture consisting of potassium osmium tetroxide dihydrate (68 μg, 0.00018 mmol) and water (68 μL). The reaction mixture was stirred overnight in the dark at room temperature. HPLC (Gemini C18, 110 {acute over (Å)}, 5μ, 250×4.6 mm, 1 mL/min, 5/95/0.05→50/50/0.05 ACN/H2O/TFA) showed complete disappearance of starting material. The reaction mixture was placed in the freezer overnight and the desired product isolated the following day by prep HPLC (Gemini C18, 110 {acute over (Å)}, 10μ, 250×21.2 mm, 20 mL/min, 5/95/0.05→50/50/0.05 ACN/H2O/TFA)—split peak collected at about 20.5 min. The relevant fractions were combined and concentrated to afford the title intermediate (1 mg, 50% yield) as a clear solid; LC/MS ESI+ m/z 624, ESI− m/z 622.

Workup

  1. customwas placed in the freezer overnight

Sources & evidence

ORD record
ord-5a7938f65b804459a023e27d3158c143
Source dataset
uspto-grants-2015_09
Patent number
US09120820B2

Reaction notes

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