Hydrochloric Acid → HCID 68635424, compound

HRID 85404Notes

Reaction equation

HRID 85404 reaction equation
Cl.[NH2:2][C:3]([CH3:17])([CH3:16])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:42](O)(=[O:50])[C:43]1[C:44](=[CH:46][CH:47]=[CH:48][CH:49]=1)[OH:45].CCN(C(C)C)C(C)C>CC#N>[OH:45][C:44]1[CH:46]=[CH:47][CH:48]=[CH:49][C:43]=1[C:42]([NH:2][C:3]([CH3:17])([CH3:16])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:50]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 338Salicylic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15236683Benzyl (2-amino-2-methylpropyl)carbamate

Product 1

HCID 68635424HCID 68635424, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The HCl salt of benzyl 2-amino-2-methylpropylcarbamate (1.0 g, 3.87 mmol) was taken up in CH3CN (15 mL) along with HATU (1.60 g, 4.2 mmol), salicylic acid (535 mg. 3.87 mmol) and DIEA (2.0 mL, 11.6 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by chromatography (30% EtOAc/pentane) to afford benzyl 2-(2-hydroxybenzamido)-2-methylpropylcarbamate (340 mg, 26%). Mass calculated for C19H22N2O4: 342.16; found: [M+H]+=343.

Workup

  1. customThe resulting reaction mixture
  2. concentrationIt was then concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with saturated aqueous NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography (30% EtOAc/pentane)

Sources & evidence

ORD record
ord-a6235f614ee44d2c907dd479bd36507d
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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