Pyridine → HCID 53793433, compound

HRID 480579Notes

Reaction equation

HRID 480579 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1CCC(N=C=NC2CCCCC2)CC1.[C:35](=[N:38]O)([NH2:37])[CH3:36].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([C:17]1[O:19][N:38]=[C:35]([CH3:36])[N:37]=1)[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 30926N-HydroxyacetamidineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 53793433HCID 53793433, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-Boc-L-phenylalanine (2.0 g, 7.5 mmol) in CH2Cl2 (20 mL) at 0° C. was added DCC (780 mg, 3.8 mmol) in CH2Cl2 (20 mL) via cannula. The reaction mixture was stirred for 1 h, the precipitate filtered off, and the filterate concentrated to dryness. Acetamidoxime (195 mg, 2.64 mmol) and pyridine (20 mL) were added and the reaction mixture heated at reflux for 1.5 h and then at RT for 16 h. The reaction mixture was poured into EtOAc (50 mL) and washed with 10% citric acid (3×25 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by column chromatography (25% EtOAc/hex) furnished (R)-[1-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-phenylethyl]carbamic acid tertbutyl ester (790 mg, 99% yield). 304.22, M+H.

Workup

  1. filtrationthe precipitate filtered off
  2. concentrationthe filterate concentrated to dryness
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux for 1.5 h
  5. waitat RT for 16 h
  6. washwashed with 10% citric acid (3×25 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by column chromatography (25% EtOAc/hex)

Sources & evidence

ORD record
ord-2247723af9804da6b0d9ca3bb7e03739
Source dataset
uspto-grants-2003_11
Patent number
US06653304B2

Reaction notes

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