Triethylamine → (S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1791371Notes

Reaction equation

HRID 1791371 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C(N(CC)CC)C.[C:31]([C:33]1[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([NH:38]O)=[NH:37])#[N:32]>C1COCC1.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:15][N:38]=[C:36]([C:35]2[CH:40]=[CH:41][CH:42]=[C:33]([C:31]#[N:32])[CH:34]=2)[N:37]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 178509779HCID 178509779, compound

Product 1

HCID 69619344(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (698 mg, 44%) was prepared according to the procedure in Example 25 from (S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1.00 g, 4.66 mmol) with isobutyl chloroformate (0.64 mL, 4.9 mmol) and triethylamine (1.6 mL, 11.5 mmol) in THF (14 mL). Then 3-cyano-N-hydroxy-benzamidine (753 mg, 4.67 mmol) and DMF (15 mL) were added and the mixture was heated at 120° C. for 18 h.

Sources & evidence

ORD record
ord-03587de826fc494386ac1305b85cf946
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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