Hydrochloric Acid → HCID 89705109, compound

HRID 528692Notes

Reaction equation

HRID 528692 reaction equation
[O:1]=[C:2]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[B:22]1[O:26][C@@H]2CC3CC([C@]2(C)[O:23]1)C3(C)C)[CH2:3][NH:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)=[O:6].Cl.C1(OB(O)O)C=CC=CC=1.COC(C)(C)C>O>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([C:5]([NH:4][CH2:3][C:2]([N:17]2[CH2:21][CH2:20][CH2:19][C@H:18]2[B:22]([OH:26])[OH:23])=[O:1])=[O:6])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 78412Phenyl dihydrogen orthoborateHCID 89705260HCID 89705260, compound

Product 1

HCID 89705109HCID 89705109, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of the N-(2-oxo-2-((2R)-2-((3aS,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide (0.27 g, 0.585 mmol) in water (8 mL) at pH=3 (adjusting as necessary with 2N aq HCl) was added phenylboric acid (0.143 g, 1.17 mmol) and methyl-tert-butylether (7 mL). The mixture was stirred for 2 days (pH was 4) water and organic layer were separated, the water layer was adjusted to pH 3, and the water layer was extracted with a mixture 4-1 of DCM-isopropanol. The DCM layer was dried over sodium sulfate, filtrated evaporated and further purified using column chromatography (DCM-MeOH 0-10% MeOH) to yield a clear oil of 0.119 g (79%) (R)-1-(2-(quinoline-4-carboxamido)acetyl)pyrrolidin-2-ylboronic acid.

Workup

  1. customwere separated
  2. extractionthe water layer was extracted with a mixture 4-1 of DCM-isopropanol
  3. dry with materialThe DCM layer was dried over sodium sulfate
  4. filtrationfiltrated
  5. customevaporated
  6. customfurther purified

Sources & evidence

ORD record
ord-835c509a9eb14c9e944391825519731e
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

Loading…