Hydrochloric Acid → HCID 89544879, compound

HRID 2283408Notes

Reaction equation

HRID 2283408 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[C:19]([F:37])=[C:20]([C@@H:25]([CH:34]3[CH2:36][CH2:35]3)[NH:26]C(=O)OC(C)(C)C)[CH:21]=[CH:22][C:23]=2[Cl:24])=[O:17])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.Cl>O1CCOCC1>[ClH:24].[NH2:26][C@H:25]([CH:34]1[CH2:36][CH2:35]1)[C:20]1[C:19]([F:37])=[C:18]([C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=2)=[O:17])[C:23]([Cl:24])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131733521HCID 131733521, compound

Product 1

HCID 89544879HCID 89544879, compoundYield 155.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Step 3 tert-Butyl N—[(R)-{3-[(4-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)carbonyl]-4-chloro-2-fluorophenyl}(cyclopropyl)methyl]carbamate (265 mg, 0.48 mmol) was treated with a 4M hydrogen chloride solution in 1,4-dioxane (5 ml) at room temperature for 60 minutes. Material that had precipitated out was re-dissolved by the addition of methanol before the mixture was concentrated in vacuo. The residue was re-concentrated from methanol before the addition of a small amount of ethyl acetate and diethyl ether to elicit precipitation. The solids were collected by filtration and were dried in a vacuum oven furnishing [4-({3-[(R)-amino(cyclopropyl)methyl]-6-chloro-2-fluorophenyl}carbonyl)phenyl]methanol hydrochloride as a white solid (138 mg)

Workup

  1. customMaterial that had precipitated out
  2. dissolutionwas re-dissolved by the addition of methanol before the mixture
  3. concentrationwas concentrated in vacuo
  4. concentrationThe residue was re-concentrated from methanol before the addition of a small amount of ethyl acetate and diethyl ether
  5. customprecipitation
  6. filtrationThe solids were collected by filtration
  7. customwere dried in a vacuum oven

Sources & evidence

ORD record
ord-a42a7c03dd98460d9dd3159f197c860b
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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