tert-Butyl isocyanate → 1-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butylaminocarbonyl]-hydrazine

HRID 1291791Notes

Reaction equation

HRID 1291791 reaction equation
[OH:1][C@H:2]([C@@H:13]([NH:21][C:22](=[O:41])[C@H:23]([CH2:37][C:38](=[O:40])[NH2:39])[NH:24][C:25]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)=[O:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][N:4]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[NH2:5].[C:42]([N:46]=[C:47]=[O:48])([CH3:45])([CH3:44])[CH3:43]>C1COCC1>[OH:1][C@H:2]([C@@H:13]([NH:21][C:22](=[O:41])[C@H:23]([CH2:37][C:38](=[O:40])[NH2:39])[NH:24][C:25]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)=[O:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][N:4]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[NH:5][C:47]([NH:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:48]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 106505161-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparagyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-hydrazine

Product 1

HCID 697830951-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butylaminocarbonyl]-hydrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a protective gas atmosphere, 100 mg (0.178 mmol) of 1-[2(S)-hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]hydrazine (Example 71E) i)) are dissolved in 0.7 ml of THF and reacted with 19 μl (0.169 mmol) of tert-butyl-isocyanate for 17 h at RT. The reaction mixture is concentrated by evaporation, the residue is dissolved in ethyl acetate and washed with 5% citric acid solution, water and brine, and the inorganic phases are extracted twice with ethyl acetate, dried with Na2SO4 and concentrated by evaporation. Column chromatography (SiO2, ethyl acetate/ethanol 10:1) yields the title compound: TLC Rf (F')=0.16; tRet (V)=15.3 min; FAB-MS (M+H)+ =660.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with 5% citric acid solution, water and brine
  4. extractionthe inorganic phases are extracted twice with ethyl acetate
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1e92ce94a3fd422fb1a44e7265fdee8b
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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