Hydrochloric Acid → HCID 53323732, compound

HRID 1966894Notes

Reaction equation

HRID 1966894 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[N:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:21](Cl)(=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].Cl>N1C=CC=CC=1>[C:17]([C:14]1[S:13][C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[N:16][N:15]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10811GlybuthiazolHCID 66982Decanoyl chloride

Product 1

HCID 53323732HCID 53323732, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

Compound 113 (250 mg, 0.80 mmol) was suspended in pyridine (1.5 mL). Decanoyl chloride (122 mg, 0.64 mmol) was added slowly at 0° C. The reaction mixture was then heated to 95° C. and was stirred for 1 h. The reaction mixture was then added to aqueous 3 N HCl solution (4 mL) and the mixture extracted with ethyl acetate (3×10 mL). The organic extracts were washed with water (3×20 mL), brine (3×20 mL), dried over anhydrous Na2SO4, and filtered. Evaporation of the solvent left a residue which was crystallized from hexanes and ethyl acetate (1:2) to give the product (294 mg, 0.63 mmol, 98%) as a solid, mp 156-157° C.; 1H NMR (500 MHz, DMSO) δ 0.80 (3, t, J=7.0 Hz), 1.15-1.33 (21, m), 1.56 (2, t, J=7.0 Hz), 2.32 (3, t, J=7.0 Hz), 7.74 (2, d, J=8.0 Hz), 7.77 (2, d, J=8.0 Hz), 10.21 (1, s), 13.90 (1, s); 13C NMR (125 MHz, DMSO): δ 13.9, 22.1, 25.0, 28.6, 28.7, 28.8, 28.9, 29.3, 31.1, 36.0, 36.5, 118.6, 126.9, 135.7, 142.9, 167.0, 167.2, 171.9; MS (LCQ, ESI+) Calculated for C22H35N4O3S2 467.2, found 467.2 (M+H)+; HRMS (FAB+, m/z) Calculated for C22H35N4O3S2 467.2151, found 467.2131 (M+H)+.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×10 mL)
  2. washThe organic extracts were washed with water (3×20 mL), brine (3×20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customEvaporation of the solvent
  6. waitleft a residue which
  7. customwas crystallized from hexanes and ethyl acetate (1:2)

Sources & evidence

ORD record
ord-db331616205741c9b58d0938b82cae68
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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