Triethylamine → HCID 67507416, compound

HRID 1829096Notes

Reaction equation

HRID 1829096 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](O)[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]#[N:22])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:25](CC)CC)C>CN(C=O)C>[NH2:25][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[C:21]#[N:22])=[O:15])[CH2:10]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67507184HCID 67507184, compound

Product 1

HCID 67507416HCID 67507416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-((2S,4R)-1-tert-Butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl)-2-cyanopyrrolidine (title compound of Reference Example 2, 60.7 g) and triethylamine (30.1 mL) were dissolved in DMF (300 mL). Methanesulfonyl chloride (16 mL) was added thereto under ice-cooling. After stirring at room temperature for 3 hr, the reaction mixture was washed with water and dried. The solvent was evaporated under reduced pressure. Ethanol was added to the residue to give (S)-1-((2S,4R)-1-tert-butoxycarbonyl-4-methanesulfonyloxy-2-pyrrolidinylcarbonyl)-2-cyanopyrrolidine (64.1 g) as a white solid.

Sources & evidence

ORD record
ord-90b84e7bbbfa4ca787969c02d7d69eac
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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