Hydrochloric Acid → HCID 90112711, compound

HRID 1500230Notes

Reaction equation

HRID 1500230 reaction equation
[CH:1]1([C@@:4]2([CH2:11][NH:12]C(=O)OC(C)(C)C)[C:8](=[O:9])[NH:7][C:6](=[O:10])[NH:5]2)[CH2:3][CH2:2]1.[ClH:20]>CO.O1CCOCC1.C1(C)C=CC=CC=1>[ClH:20].[NH2:12][CH2:11][C@@:4]1([CH:1]2[CH2:2][CH2:3]2)[NH:5][C:6](=[O:10])[NH:7][C:8]1=[O:9]

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 90111597HCID 90111597, compound

Product 1

HCID 90112711HCID 90112711, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
25 °C

Procedure

tert-butyl N-[[(4R)-4-cyclopropyl-2,5-dioxo-imidazolidin-4-yl]methyl]carbamate (310 g, 1151 mmol) is dissolved in MeOH (3.1 L) at 6° C. 4M HCl in dioxane (310 mL) is added and the mixture warmed to 25° C. After stirring for 22 h, a second portion of 4M HCl in dioxane (110 mL) is added and stiffing continued for an additional 16 h. The reaction is then allowed to sit with no agitation for 2 days. The mixture is then diluted with toluene (6 L). The title compound is collected by filtration of the mixture as a white solid (180 g).

Workup

  1. waitstiffing continued for an additional 16 h
  2. waitto sit with no agitation for 2 days
  3. filtrationThe title compound is collected by filtration of the mixture as a white solid (180 g)

Sources & evidence

ORD record
ord-410e78222e974309bba787e3767190a9
Source dataset
uspto-grants-2015_12
Patent number
US09206139B2

Reaction notes

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