Methanol → HCID 53234366, compound

HRID 1256083Notes

Reaction equation

HRID 1256083 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21]C(=O)C(F)(F)F)=[CH:17][C:16]=3[CH2:28][CH2:29][C:30](OCC)=[O:31])(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.[BH4-].[Na+].CO>C1COCC1>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)(=[O:13])=[O:14])=[C:16]([CH2:28][CH2:29][CH2:30][OH:31])[CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 53234295HCID 53234295, compound

Product 1

HCID 53234366HCID 53234366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 3-(2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)propanoate (1.6 g, 3.2 mmol), and NaBH4 (0.48 g, 12.8 mmol) in THF (30 mL) was stirred at 0° C. Then CH3OH (1 ml) was added dropwise into the mixture and stirred at r.t. overnight. The solvent was evaporated and the residue was extracted with EtOAc, washed with brine, dried over Na2SO4 and concentrated to give the crude product. The residue was purified by prep-HPLC (column: YMC 150×30.0 mm, 20μ; liquid phase: [A-H2O; B-MeCN+0.1% TFA] B %: 12%-42%, 10 min) to give the title compound, which was dissolved in MeCN, acidified with aq. HCl and freeze-dried to give the product as hydrochloride salt (280 mg, yield 70%). 1H NMR (400 MHz, DMSO-d6): δ9.97 (s, 1H), 7.57-7.09 (m, 6H), 4.83 (s, 2H), 3.46-3.42 (m, 2H), 2.83-2.79 (m, 2H), 1.66-1.62 (m, 2H); ESI-MS m/z 385 (M+Na, positive); HPLC purity: 94.25% (MaxPlot 190-370 nm), 94.25% (220 nm).

Workup

  1. stirringstirred at r.t. overnight
  2. customThe solvent was evaporated
  3. extractionthe residue was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe residue was purified by prep-HPLC (column: YMC 150×30.0 mm, 20μ; liquid phase: [A-H2O; B-MeCN+0.1% TFA] B %: 12%-42%, 10 min)

Sources & evidence

ORD record
ord-cd2d1e4715ca4e658e956e0fe808b4b2
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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