Ammonium Hydroxide → HCID 58226539, compound

HRID 1429250Notes

Reaction equation

HRID 1429250 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][CH3:14])[CH2:10][C@H:9]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([N:21]=C=NCCCN(C)C)C.O.N1(O)C2C=CC=CC=2N=N1.[OH-].[NH4+]>C(#N)C>[C:15]([C@@H:9]1[CH2:10][C@H:11]([O:13][CH3:14])[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:17])[NH2:21]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15222286(4S)-1-(tert-Butoxycarbonyl)-4-methoxy-L-proline

Product 1

HCID 58226539HCID 58226539, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2S,4S)-1-(tert-Butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid (2.9 g, 11.82 mmol) was dissolved in acetonitrile (150 mL) and cooled in an ice bath. N1-((Ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (2.72 g, 14.19 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol hydrate (2.17 g, 14.19 mmol) were added, and the mixture was stirred at ambient temperature for 15 hours, becoming clear. 28% Ammonium hydroxide (4.93 mL, 35.5 mmol) was added dropwise resulting in a precipitate. After stirring for 2 hours, then mixture was concentrated, diluted with water and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 100% yield of (2S,4S)-tert-butyl 2-carbamoyl-4-methoxypyrrolidine-1-carboxylate as a white waxy solid.

Workup

  1. temperaturecooled in an ice bath
  2. customresulting in a precipitate
  3. stirringAfter stirring for 2 hours
  4. concentrationmixture was concentrated
  5. additiondiluted with water
  6. extractionextracted into ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a1a6c8555d904c86acf966990d2aedd7
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

Loading…