Hydrochloric Acid → HCID 178472733, compound

HRID 576566Notes

Reaction equation

HRID 576566 reaction equation
[CH2:1]([O:3][C:4](=[O:62])[CH2:5][N:6]([C:8](=[O:61])[C@@H:9]([NH:25][C:26](=[O:60])[C@@H:27]([NH:52]C(OC(C)(C)C)=O)[CH2:28][CH2:29][CH2:30][NH:31]/[C:32](/[NH2:51])=[N:33]\[S:34]([C:37]1[C:38]([CH3:50])=[C:39]([CH3:49])[C:40]2[O:44][C:43]([CH3:46])([CH3:45])[CH2:42][C:41]=2[C:47]=1[CH3:48])(=[O:36])=[O:35])[CH2:10][N:11]([CH3:24])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[CH3:7])[CH3:2].Cl>C(Cl)Cl.O1CCOCC1>[CH2:1]([O:3][C:4](=[O:62])[CH2:5][N:6]([C:8](=[O:61])[C@@H:9]([NH:25][C:26](=[O:60])[C@@H:27]([NH2:52])[CH2:28][CH2:29][CH2:30][NH:31]/[C:32](/[NH2:51])=[N:33]\[S:34]([C:37]1[C:38]([CH3:50])=[C:39]([CH3:49])[C:40]2[O:44][C:43]([CH3:45])([CH3:46])[CH2:42][C:41]=2[C:47]=1[CH3:48])(=[O:35])=[O:36])[CH2:10][N:11]([CH3:24])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[CH3:7])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178472732HCID 178472732, compound

Product 1

HCID 178472733HCID 178472733, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound E (7.4 g, 8.2 mmol) in DCM (24 mL) was treated with 4 M HCl in dioxane (24 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 h. DCM and most of the dioxane were removed in vacuo to a total volume of ˜15 mL, and Et2O (300 mL) was added. Precipitated product was filtered off, washed with Et2O (150 mL) and hexane and finally dried in vacuo to afford compound F (6.34 g, 100% yield) as a cream solid. LC-MS [M+H] 811.4 (C34H50N8O11S2+H, calc: 811.94). Purity >95% (UV/254 nm). Compound F was used without further purification.

Workup

  1. customDCM and most of the dioxane were removed in vacuo to a total volume of ˜15 mL, and Et2O (300 mL)
  2. additionwas added
  3. filtrationPrecipitated product was filtered off
  4. washwashed with Et2O (150 mL) and hexane
  5. customfinally dried in vacuo

Sources & evidence

ORD record
ord-eee8e31a1bcb4c498ef7064870e46596
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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