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Hydrazine → methyl N-[(1S)-1-[[[(2S,3S)-3-[[(2S)-4-amino-4-oxo-2-(quinoline-2-carbonylamino)butanoyl]amino]-2-hydroxy-4-phenyl-butyl]-(cyclohexylmethyl)amino]carbamoyl]-2-methyl-propyl]carbamate

HRID 1291790
Notes
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Reaction equation

HRID 1291790 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].[CH3:42][O:43][C:44]([NH:46][C@H:47]([C:51](O)=[O:52])[CH:48]([CH3:50])[CH3:49])=[O:45].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NN>CN1CCOCC1.CN(C=O)C.CN1CCOCC1.CN(C=O)C>[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:51](=[O:52])[C@H:47]([CH:48]([CH3:49])[CH3:50])[NH:46][C:44]([O:43][CH3:42])=[O:45]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 9321HydrazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 106505161-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparagyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-hydrazineHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid2×

Product 1

HCID 461985
methyl N-[(1S)-1-[[[(2S,3S)-3-[[(2S)-4-amino-4-oxo-2-(quinoline-2-carbonylamino)butanoyl]amino]-2-hydroxy-4-phenyl-butyl]-(cyclohexylmethyl)amino]carbamoyl]-2-methyl-propyl]carbamate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 79724-MethylmorpholineSolventHCID 19048625Dmf nmmSolvent

Procedure

Under a nitrogen 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)) and 34 mg (0.196 mmol) of N-methoxycarbonyl-(L)-valine (Example 73b) are dissolved in 1.75 ml of a 0.3M solution of NMM in DMF, 74 mg (0.196 mmol) of HBTU are added and the mixture is stirred at RT. Since, after 3 days, there is still unreacted hydrazine present, a further 0.3 equivalents in each case of N-methoxycarbonyl-(L)-valine and HBTU in 0.48 ml of 0.3M NMM/DMF is added. After 18 h the reaction mixture is concentrated by evaporation under HV, the residue is dissolved in methylene chloride and washed with saturated NaHCO3 solution, water and brine, the aqueous phases are extracted twice with methylene chloride, and the organic phases are dried with Na2SO4 and concentrated by evaporation. Column chromatography (SiO2, methylene chloride/methanol 15:1) and digestion from DIPE yields the title compound: TLC Rf (A')=0.17; tRet (V)=14.6 min; FAB-MS (M+H)+ =718.

Workup

  1. additionare added
  2. concentrationAfter 18 h the reaction mixture is concentrated by evaporation under HV
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washwashed with saturated NaHCO3 solution, water and brine
  5. extractionthe aqueous phases are extracted twice with methylene chloride
  6. dry with materialthe organic phases are dried with Na2SO4
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5b2e95c38d0445179ed72ce016bd50f0
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753652

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes