Water → HCID 86225047, compound

HRID 2389509Notes

Reaction equation

HRID 2389509 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[C:16]([O:20][C:21](=[O:24])[CH2:22][NH2:23])([CH3:19])([CH3:18])[CH3:17].C([O-])(O)=O.[Na+].O>CS(C)=O>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[NH:23][CH2:22][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:24])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 516892Sodium BicarbonateHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 86225047HCID 86225047, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-fluoro-3-nitrobenzotrifluoride (209 mg, 1 mmol), glycine tert-butyl ester hydrochloride (201 mg, 1.2 mmol) and NaHCO3 (128 mg, 2 mmol) in dry DMSO (1 ml) is stirred overnight at 50 or 65° C. In case the reaction is not complete a further heating at 85° C. to 100° C. for 3 h is necessary. The reaction is then cooled to rt and water is added. The yellow to orange solid formed is filtered over a fritted funnel, rinsed thoroughly with water and dried under high vacuum. This yields the title compound (254 mg) in 79% as a yellow solid: tR=1.08 min (LC-3), ESI-MS (pos.): m/z 403.2 [M+2AcCN]+, m/z 321.56 [M+H]+, 1H-NMR (DMSO-d6): δ (ppm) 1.44 (s, 9H, tBu), 4.23 (d, 2H, NHCH2CO2), 7.08 (d, 1H, Harom), 7.80 (dd, 1H, H, m), 8.34 (br. s, 1H, Harom), 8.65 (t, 1H, NH).

Workup

  1. temperaturea further heating at 85° C. to 100° C. for 3 h
  2. temperatureThe reaction is then cooled to rt
  3. customThe yellow to orange solid formed
  4. filtrationis filtered over a fritted funnel
  5. washrinsed thoroughly with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-0d1a6c7a99e04dffb57013ccfbd9d7ca
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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