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TERT-BUTYL TRICHLOROACETATE → tert-Butyl 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetate

HRID 1256113
Notes
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Reaction equation

HRID 1256113 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.ClC(Cl)(Cl)C(O[C:31]([CH3:34])([CH3:33])[CH3:32])=O>C1COCC1.C(Cl)Cl.CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:24])(=[O:25])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([O:11][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:10])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 4405255TERT-BUTYL TRICHLOROACETATEHCID 53234452HCID 53234452, compound

Product 1

HCID 68300728tert-Butyl 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetate

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To the solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (2.2 g, 6 mmol) in dry THF (20 ml) under nitrogen, added the solution of tert-butyl 2,2,2-trichloroacetate (4.3 ml, 24 mmol) in dry DCM (10 ml), followed by BF3Et2O (0.1 ml, 0.72 mmol). The reaction was stirred at rt overnight. Quenched the reaction with sodium bicarbonate (sat. in water), diluted with EtOAc, washed with 1N HCl, water and brine, dried over anhydrous sodium sulfate. Concentrated, the result was purified by flash chromatography with EtOAc and hexane. Got 650 mg light yellow solid as product. MS calcd for (C19H23BN2O6S): 418.14. MS found (ESI negative): (M−H)−=417.0. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.83 (s, 1H), 7.46 (d, J=8.8 Hz, 1H), 7.40 (d, J=1.6 Hz, 1H), 7.19 (d, J=8 Hz, 1H), 7.09 (dd, J=8 Hz, 1H), 6.39 (d, J=6.8 Hz, 1H), 6.37 (s, 1H), 4.84 (s, 2H), 3.77 (s, 2H), 1.37 (s, 9H).

Workup

  1. customQuenched
  2. customthe reaction with sodium bicarbonate (sat. in water)
  3. washwashed with 1N HCl, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentrated
  6. customthe result was purified by flash chromatography with EtOAc and hexane

Sources & evidence

ORD record
ord-9d00be5d632d4cdda571d8e6305d3b24
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461134B2

Reaction notes

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