Acetic Anhydride → HCID 58292652, compound

HRID 1798279Notes

Reaction equation

HRID 1798279 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[S:14][C:15]([C:18](=[NH:21])[NH:19]O)=[CH:16][N:17]=3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:3]1.C(OC(=O)C)(=O)C>C(O)(=O)C.[Pd]>[C:18]([C:15]1[S:14][C:13]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[CH:4]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[N:17][CH:16]=1)(=[NH:19])[NH2:21]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178470806HCID 178470806, compound

Product 1

HCID 58292652HCID 58292652, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of crude ethyl 2-(1-hydroxy-6-(5-(N-hydroxycarbamimidoyl)thiazol-2-yloxy)-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (6.2 g crude) in 30 ml of acetic acid was added 400 ul of acetic anhydride. After the mixture was stirred at room temperature for one and half hour, it was treated with palladium (10% wet on charcoal, 1.8 g) and then hydrogenation on Parr-shaker for five hours. The mixture was filtered through a Celite pad and the filtrate was concentrated and dried under hi-Vac to give the crude product. The crude was used in subsequent steps without further purification.

Workup

  1. waithydrogenation on Parr-shaker for five hours
  2. filtrationThe mixture was filtered through a Celite pad
  3. concentrationthe filtrate was concentrated
  4. customdried under hi-Vac

Sources & evidence

ORD record
ord-4a28d023429144ac95170024eeb8ac7f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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