Ammonia → N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-prolinamide

HRID 1282960Notes

Reaction equation

HRID 1282960 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=O)=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.[NH3:42]>O1CCCC1.C(N(CC)CC)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:42])=[O:27])=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 62365Isobutyl chloroformateHCID 54515815N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-proline

Product 1

HCID 53756909N-[(Benzyloxy)carbonyl]-L-isoleucyl-L-prolyl-L-prolinamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Benzyloxycarbonyl-isoleucyl-prolyl-proline (4.5 g) is dissolved in a mixture of tetrahydrofuran (30 ml) and triethylamine (1.4 ml). The solution is chilled in a -5° cooling bath and isobutyl chloroformate (1.6 ml) is added. The solution is allowed to warm to room temperature (10 minutes) and concentrated aqueous ammonia (10 ml) is added. After four hours stirring at room temperature, the reaction is concentrated in vacuo, diluted with ethyl acetate and washed sequentially with saturated sodium bicarbonate, water, 0.1 N hydrochloric acid and water. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo to give the title compound.

Workup

  1. temperatureThe solution is chilled in a -5°
  2. temperaturecooling bath
  3. additionis added
  4. concentrationthe reaction is concentrated in vacuo
  5. additiondiluted with ethyl acetate
  6. washwashed sequentially with saturated sodium bicarbonate, water, 0.1 N hydrochloric acid and water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-ba999c62b81b408e83dcc33283325721
Source dataset
uspto-grants-1976_08
Patent number
US03973006

Reaction notes

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