Citric Acid → HCID 66980903, compound

HRID 1254657Notes

Reaction equation

HRID 1254657 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:12][C@@H:13]([C:16]([OH:18])=[O:17])[CH2:14][OH:15].C([O-])([O-])=O.[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:12][C@H:13]([CH2:14][OH:15])[C:16]([OH:18])=[O:17])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 71077D-SerineHCID 445509712-Chloro-4-fluoro-3-methylbenzonitrile

Product 1

HCID 66980903HCID 66980903, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

2-chloro-4-fluoro-3-methylbenzonitrile (500 mg, 2.95 mmol) was mixed together with H-D-Ser-OH (682 mg, 6.49 mmol) in DMSO (20 mL). K2CO3 (856 mg, 6.19 mmol) was added to the reaction mixture and stirred at 75° C. for 24 h. The reaction mixture was cooled to room temperature and poured slowly in to a 10% citric acid solution and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times to get the crude product. The crude product was chromatographed with a gradient of hexanes/EtOAc and then with EtOAc, 100% to give the final product (220 mg): 1H NMR (500 MHz, DMSO-d6, δ in ppm) 7.47 (d, J=9 Hz, 1H), 6.57 (d, J=9 Hz, 1H), 6.13 (br s, 1H), 3.62 (m, 2H), 2.18 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred for 10 min at room temperature
  3. extractionThe solution was extracted with EtOAc several times
  4. customto get the crude product
  5. customThe crude product was chromatographed with a gradient of hexanes/EtOAc

Sources & evidence

ORD record
ord-78277b3677cf4f5a8a7e1482c1b28eb2
Source dataset
uspto-grants-2013_06
Patent number
US08455525B2

Reaction notes

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