Ammonia → HCID 66756556, compound

HRID 1642664Notes

Reaction equation

HRID 1642664 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:23]([CH2:24][CH3:25])[CH2:22][CH2:21][C@H:17]1[C:18](O)=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:28](CC)CC)C.ClC(OCC)=O.N>C1COCC1.O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:23]([CH2:24][CH3:25])[CH2:22][CH2:21][C@H:17]1[C:18]([NH2:28])=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66756932HCID 66756932, compound

Product 1

HCID 66756556HCID 66756556, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(tert-butoxycarbonyl)-L-leucyl-(5S)-5-ethyl-L-proline was mixed with triethylamine (0.426 mL, 3.25 mmol) in THF (4 mL) and cooled to 0° C. followed by the addition of ethyl chloroformate (0.287 mL, 3.0 mmol). After 20 minutes, 0.5 M ammonia in dioxane (6 mL) was added. After 4 hours, the mixture was concentrated, and the residue was partitioned between 1 N HCl and ethyl acetate. The organic extracts were washed with saturated NaHCO3, dried (Na2SO4), filtered, concentrated under reduced pressure and purified by flash chromatography (80% to 100% ethyl acetate/hexane) to provide the titled compound. MS (ESI) m/z 356 (M+H)+.

Workup

  1. waitAfter 4 hours
  2. concentrationthe mixture was concentrated
  3. customthe residue was partitioned between 1 N HCl and ethyl acetate
  4. washThe organic extracts were washed with saturated NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by flash chromatography (80% to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9686ddb66abe4647bc79939ed444367b
Source dataset
uspto-grants-2012_02
Patent number
US08119664B2

Reaction notes

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