Ethyl 2-(1-hydroxy-4-methyl-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate → Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate

HRID 1798311Notes

Reaction equation

[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[S:14][C:15]([N+:18]([O-])=O)=[N:16][N:17]=3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:3]1>C(O)C.O.Cl.[Fe]>[NH2:18][C:15]1[S:14][C:13]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[CH:4]([CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[N:17][N:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Into a 50-mL round-bottom flask was placed a solution of ethyl 2-(1-hydroxy-4-methyl-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate (500 mg, 1.15 mmol, 1.00 equiv, 90%) in ethanol/H2O (15/5 mL). This was followed by the addition of Fe (280 mg, 5.00 mmol, 4.00 equiv). Then added 2 drops of HCl. The resulting solution was stirred for 2 h at 85° C. The reaction mixture was cooled and filtered. The filtrate was concentrated under vacuum. This resulted in 0.8 g (90%) of ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate as a brown solid.

Workup

customInto a 50-mL round-bottom flask was placed
temperatureThe reaction mixture was cooled
filtrationfiltered
concentrationThe filtrate was concentrated under vacuum
customThis resulted in 0.8 g (90%) of ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate as a brown solid

Sources & evidence

ORD record: ord-bd877e39687d4066a9e4c6c48ad2f060
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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