Hydrochloric Acid → HCID 178486315, compound

HRID 494031Notes

Reaction equation

HRID 494031 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@:9]3([O:38][CH3:39])[CH2:10][CH2:11][C@H:12]2[N:20](C(OC(C)(C)C)=O)[C:21]([NH:23]C(OC(C)(C)C)=O)=[NH:22])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([OH:40])[CH:4]=[CH:5]2.[ClH:41]>CCOCC.O>[ClH:41].[ClH:41].[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@:9]3([O:38][CH3:39])[CH2:10][CH2:11][C@H:12]2[NH:20][C:21]([NH2:23])=[NH:22])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([OH:40])[CH:4]=[CH:5]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 141603152HCID 141603152, compound

Product 1

HCID 178486315HCID 178486315, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of Compound 16 (50 mg, 0.089 mmol) in Et2O (3 ml) was mixed through to a clear acidic reaction with ethereal HCl and with 4 drops of H2O. The mixture was subjected to ultrasound for one hour at room temperature and then evaporated. The residue (40 mg of white foam resin) was dissolved in H2O and freeze dried. Yield: 30 mg (79%) 17.2 HCl as white lyophilisate: 1H-NMR (CDCl3): δ 9.59 (s, OH—C(3)); 9.29 (s, br, NH+); 8.53 (d, J=8.0, C(6)-NH—); 7.29 (s, br, C(6)-NH—C(NH2)2+), 6.78 (d, J=8.1, 1 arom. H); 6.69 (d, J=8.1, 1 arom. H); 4.49 (d, J=7.2, H—C(5)); 3.26 (s, CH3O—C(14)); 2.84 (s, CH3N).

Workup

  1. customultrasound for one hour
  2. customat room temperature
  3. customevaporated
  4. dissolutionThe residue (40 mg of white foam resin) was dissolved in H2O
  5. customfreeze dried

Sources & evidence

ORD record
ord-b516400521fa471483bd868cdbc3b033
Source dataset
uspto-grants-2009_05
Patent number
US07538118B2

Reaction notes

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