Hydrochloric Acid → HCID 118160628, compound

HRID 1048869Notes

Reaction equation

HRID 1048869 reaction equation
[C:1]([NH:4][C@H:5]([C:37]([NH2:39])=[O:38])[CH2:6][S:7][C:8](=[O:36])[C@@H:9]([NH:23][C:24](=[O:35])[CH2:25][CH2:26][NH:27]C(OC(C)(C)C)=O)[CH2:10][C:11]1[N:15](C(OC(C)(C)C)=O)[CH:14]=[N:13][CH:12]=1)(=[O:3])[CH3:2].[ClH:40]>O1CCOCC1>[ClH:40].[ClH:40].[NH2:27][CH2:26][CH2:25][C:24]([NH:23][C@@H:9]([CH2:10][C:11]1[NH:15][CH:14]=[N:13][CH:12]=1)[C:8](=[O:36])[S:7][CH2:6][C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C:37]([NH2:39])=[O:38])=[O:35]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 118160616HCID 118160616, compound

Product 1

HCID 118160628HCID 118160628, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mechanically stirring solution at room temperature under N2 of tert-butyl 5-((S)-3-((R)-2-acetamido-3-amino-3-oxopropylthio)-2-(3-(tert-butoxycarbonylamino)propanamido)-3-oxopropyl)-1H-imidazole-1-carboxylate (45d, 104.1 g, 182.4 mmol) in 1200 mL of dioxane was added dropwise hydrogen chloride, 4 N solution in dioxane (106 mL, 640 mmol). After addition of ˜50 mL of the HCl solution, solid formed. After complete addition, the sample was stirred at room temperature under N2 for 3 h, filtered and vacuum dried to give 97.9 g (>100%) of titled compound as white solid. MS (APCI) m/z 371 [parent+H]+.

Workup

  1. customformed
  2. additionAfter complete addition
  3. filtrationfiltered
  4. customvacuum dried

Sources & evidence

ORD record
ord-3a003b2ab743477280484cc473be76b3
Source dataset
uspto-grants-2016_07
Patent number
US09382211B2

Reaction notes

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