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

HRID 1291785
Notes
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Reaction equation

HRID 1291785 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C@H:14]([C:19]([OH:21])=O)[CH2:15][C:16](=[O:18])[NH2:17])=[O:12].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[OH:54][C@H:55]([C@@H:73]([NH2:81])[CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[CH2:56][N:57]([CH2:66][CH:67]1[CH2:72][CH2:71][CH2:70][CH2:69][CH2:68]1)[NH:58][C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60]>C1COCC1>[OH:54][C@H:55]([C@@H:73]([NH:81][C:19](=[O:21])[C@H:14]([CH2:15][C:16](=[O:18])[NH2:17])[NH:13][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)=[O:12])[CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[CH2:56][N:57]([CH2:66][CH:67]1[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72]1)[NH:58][C:59]([O:61][C:62]([CH3:65])([CH3:63])[CH3:64])=[O:60]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 108343151-[2(S)-hydroxy-3(S)-amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazineHCID 11044384(S)-4-Amino-4-oxo-2-(((quinolin-2-yl)carbonyl)amino)butanoic acid

Product 1

HCID 10842076
1-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 5° C., 940 mg (3.27 mmol) of quinoline-2-carbonyl-(L)-asparagine (in the form of the hydrochloride salt) are dissolved in 35 ml of THF, and 736 mg (3.57 mmol) of DCC are added. After 10 min, 482 mg (3.57 mmol) of HOBT, 0.82 ml (7.44 mmol) of NMM and 1.165 g (2.98 mmol) of 1-[2(S)-hydroxy-3(S)-amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butoxycarbonyl]-hydrazine are added and the mixture is stirred at RT for 18 h. The reaction mixture is filtered and the filtrate is concentrated by evaporation. The residue is partitioned between 3 portions of ethyl acetate, saturated NaHCO3 solution, water and brine, and the organic phases, which have been dried with Na2SO4, are concentrated by evaporation and subjected to column chromatography (SiO2, ethyl acetate) to yield the title compound: TLC Rf (O)=0.16; tRet (V)=16.5 min; FAB-MS (M+H)+ =661.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation
  3. customThe residue is partitioned between 3 portions of ethyl acetate, saturated NaHCO3 solution, water and brine
  4. dry with materialthe organic phases, which have been dried with Na2SO4
  5. concentrationare concentrated by evaporation

Sources & evidence

ORD record
ord-c3c39aa0a59443ba976649cc8dc19d4e
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