Triethylamine → 1,1-Dimethylethyl (2S,4S)-4-amino-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylate

HRID 1829099Notes

Reaction equation

HRID 1829099 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][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:23](CC)CC)C>ClCCl>[NH2:23][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][S:18][CH2:17]2)=[O:15])[CH2:10]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67506663HCID 67506663, compound

Product 1

HCID 675063191,1-Dimethylethyl (2S,4S)-4-amino-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((2S,4R)-1-tert-Butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl)-1,3-thiazolidine (title compound of Reference Example 9, 56.3 g) and triethylamine (28.5 mL) were dissolved in dichloromethane (1.0 l), and methanesulfonyl chloride (15.1 mL) was added thereto under ice-cooling. After stirring under ice-cooling for 1 hr, the reaction mixture was washed with water and dried. The solvent was evaporated under reduced pressure to give 3-((2S,4R)-1-tert-butoxycarbonyl-4-methanesulfonyloxy-2-pyrrolidinylcarbonyl)-1,3-thiazolidine (70.5 g) as an oil.

Sources & evidence

ORD record
ord-78dddf68aa6c4623b4b35063c676fe85
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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