Triethylamine → HCID 131733970, compound

HRID 710945Notes

Reaction equation

HRID 710945 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C(N(CC)CC)C.[NH:32]([C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[NH2:33]>C(Cl)Cl>[CH2:37]([O:36][C:34]([NH:32][NH:33][C:14]([C@H:9]1[CH2:10][CH2:11][C:12](=[O:13])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])=[O:35])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 79242Benzyl carbazateHCID 186455521-(tert-Butoxycarbonyl)-5-oxo-D-proline

Product 1

HCID 131733970HCID 131733970, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-1-(tert-butoxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid (1.146 g, 5.00 mmol) in dehydrated methylene chloride (25 mL) was cooled to 0° C. under an argon atmosphere and gradually added dropwise isobutyl chloroformate (0.682 g) so that the temperature does not exceed 0° C. Then, triethylamine (0.505 g) was gradually added so that the temperature does not exceed 0° C., followed by stirring 30 minutes, thereby a mixed acid anhydride was prepared in the reaction system. To this reaction mixture was gradually added benzyl hydrazinecarboxylate (0.830 g), after the addition, followed by raising the temperature to room temperature and stirring for 1 hour. This reaction mixture was washed with 0.5M hydrochloric acid and saturated brine, the organic layer was dried over magnesium sulfate and then distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane/ethyl acetate=4/1→0/1→ethyl acetate/methanol=30/1) to afford 1.53 g of the title compound (yield 80.1%).

Workup

  1. customdoes not exceed 0° C
  2. customdoes not exceed 0° C.
  3. additionafter the addition
  4. stirringstirring for 1 hour
  5. washThis reaction mixture was washed with 0.5M hydrochloric acid and saturated brine
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. distillationdistilled off under reduced pressure

Sources & evidence

ORD record
ord-48d3074824cb48a3a3dba3b1c530618b
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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