Hydrochloric Acid → HCID 10710909, compound

HRID 1274130Notes

Reaction equation

HRID 1274130 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:18][C:17]=2[N+:29]([O-:31])=[O:30])[CH2:11][CH2:10]1)=O)(C)(C)C.CO.C(Cl)Cl>O1CCOCC1>[C:25]([O:24][C:22](=[O:23])[C:19]1[CH:20]=[CH:21][C:16]([NH:15][CH:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)=[C:17]([N+:29]([O-:31])=[O:30])[CH:18]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10622083HCID 10622083, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 10710909HCID 10710909, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (1 mL, 4M in 1,4-dioxane) was added to a solution of (43) (0.1 g, 0.24 mmol) in 1,4-dioxane (5 mL) at 25° C. After 12 h, the reaction mixture was evaporated to a bright yellow solid residue which was basicified with NaOH(aq). The aqueous solution was extracted with EtOAc (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give a yellow oily residue which was used in the next reaction without further purification (0.045 g, 59%): TLC (Rf =0.20; 15% MeOH/CH2Cl2); 1H NMR (CDCl3) δ 8.74 (s, 1H), 8.33 (d, 1H, J=5.4), 7.94 (d, 1H, J=8.8), 6.82 (d, 1H, J=8.8), 3.60 (m, 1H), 3.12 (d, 2H, J=11.3), 2.74 (t, 2H, J=11.7), 2.21 (s, 2H), 2.05 (d, 2H, J=12.5), 1.53 (s, 9H); 13C NMR (CDCl3) δ 164.2, 146.3, 136.2, 131.1, 129.4, 118.9, 113.4, 81.2, 49.8, 44.8, 32.9, 28.2; HRMS (FAB) m/z 322.1750 (M+H)+ (C16H23N3O4 requires 322.1761); Anal. (C16H23N3O4 ·1HCl·1CH3OH) C, H, N.

Workup

  1. customthe reaction mixture was evaporated to a bright yellow solid residue which
  2. extractionThe aqueous solution was extracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oily residue which
  7. customwas used in the next reaction without further purification (0.045 g, 59%)

Sources & evidence

ORD record
ord-b3fc7a983f1e491e920a54351f39a91f
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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