Hydrochloric Acid → HCID 178486316, compound

HRID 494033Notes

Reaction equation

HRID 494033 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 141603155HCID 141603155, compound

Product 1

HCID 178486316HCID 178486316, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of Compound 18 (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 1.5 h at room temperature and then evaporated. The residue (40 mg of white foam resin) was dissolved in H2O and freeze dried. Yield: 35 mg (92%) 19.2 HCl as white lyophilisate: 1H-NMR (CDCl3): δ 9.29 (s, br, NH+); 9.20 (s, OH—C(3)); 7.57 (d, J=8.8, C(6)-NH—); 7.46 (s, br, C(6)-NH—C(NH2)2+), 6.76 (d, J=8.1, 1 arom. H); 6.62 (d, J=8.1, 1 arom. H); 4.70 (d, J=4.0, H—C(5)); 3.36 (s, CH3O—C(14)); 2.88 (s, CH3N).

Workup

  1. customultrasound for 1.5 h
  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-732c5d72a626458995c6bd11a5ac2a00
Source dataset
uspto-grants-2009_05
Patent number
US07538118B2

Reaction notes

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