Hydrochloric Acid → HCID 69927594, compound

HRID 536997Notes

Reaction equation

HRID 536997 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1([CH:12]([OH:22])[C:13](=[O:21])[NH:14][C:15]2[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])(C)C.Cl.C(Cl)(OCC1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=O.C([O-])(O)=O.[Na+]>O1CCOCC1.O.C(Cl)Cl>[OH:22][CH:12]([C:8]1([NH:7][C:6](=[O:23])[O:5][CH2:1][CH:4]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:35]=3[C:36]3[C:41]2=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:9][CH2:10][CH2:11]1)[C:13]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 67230308HCID 67230308, compound

Product 1

HCID 69927594HCID 69927594, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

{1-[Hydroxy-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-methyl]-cyclobutyl}-carbamic acid tert-butyl ester (209 mg, 0.64 mmol) was treated with HCl (4M in dioxane, 5 mL) overnight and then concentrated. The resulting hydrochloride salt was added to a solution of Fmoc-Cl (232 mg, 0.89 mmol) in dioxane:water 2:3, whereafter NaHCO3 (181 mg, 2.24 mmol) was added. The reaction mixture was stirred at room temperature and after for 40 min the solution was diluted with DCM and extracted. The organic phase was washed with brine, dried (NaSO4) and concentrated. Purification by flash column chromatography (EtOAc/iso-Hexane, 4:6-6:4) gave the title compound as a white solid (257 mg, 90%). MS m/z 446.9 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionwas added
  3. extractionextracted
  4. washThe organic phase was washed with brine
  5. dry with materialdried (NaSO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (EtOAc/iso-Hexane, 4:6-6:4)

Sources & evidence

ORD record
ord-63e4f8ae00324b44a36543ddfa92fafd
Source dataset
uspto-grants-2014_10
Patent number
US08859605B2

Reaction notes

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