Hydrochloric Acid → HCID 58104599, compound

HRID 588009Notes

Reaction equation

HRID 588009 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[OH:14])[CH2:9]1)=O)(C)(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[C:42]=1O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.Cl.O1CCOCC1>CCO.C1COCC1>[CH:15]1([C@H:13]([O:14][C:42]2[C:41]([Cl:40])=[CH:46][CH:45]=[CH:44][C:43]=2[Cl:47])[C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 68992,6-DichlorophenolHCID 11776TriphenylphosphineHCID 312751,4-DioxaneHCID 5363146Diisopropyl azodicarboxylateHCID 58104612HCID 58104612, compound

Product 1

HCID 58104599HCID 58104599, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-((R)-Cyclohexylhydroxymethyl)pyrrolidine-1-carboxylic acid t-butyl ester (190 mg, 670 μmol), was combined with PPh3 (79 mg, 0.3 mmol), THF (0.2 mL), and 2,6-dichlorophenol (73 mg, 0.5 mmol). DIAD (59 nL, 0.3 mmol) was added and the mixture was allowed to stand at room temperature for 2 hours. EtOH (1.0 mL) and 4.0 N HCl in dioxane (0.5 mL, 2.0 mmol) were added, and the mixture was allowed to stand at room temperature overnight. The solvent was removed under reduced pressure, and the remaining material was dissolved in 50% AcOH (6 mL) and purified by preparative HPLC (1″ C18 column; 10-50% MeCN over 1 hour). The clean fractions were pooled and lyophilized to yield the title compound as a mono-TFA salt (37 mg, 95% purity). MS m/z: [M+H]1 calcd for C17H23Cl2NO, 328.12. found 328.4.

Workup

  1. waitto stand at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe remaining material was dissolved in 50% AcOH (6 mL)
  4. custompurified by preparative HPLC (1″ C18 column
  5. wait10-50% MeCN over 1 hour)

Sources & evidence

ORD record
ord-baa69ffb22844b5badb521369e66471d
Source dataset
uspto-grants-2016_01
Patent number
US09227933B2

Reaction notes

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