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4-Methylmorpholine → methyl N-[(1S)-1-[[(1S,2S)-1-benzyl-3-[[4-(2-tert-butyltetrazol-5-yl)phenyl]methyl-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethyl-butanoyl]amino]amino]-2-hydroxy-propyl]carbamoyl]-2-methyl-propyl]carbamate

HRID 380223
Notes
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Reaction equation

HRID 380223 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10](O)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.CN1CCOCC1.Cl.[C:41]([N:45]1[N:49]=[N:48][C:47]([C:50]2[CH:55]=[CH:54][C:53]([CH2:56][N:57]([NH:70][C:71](=[O:82])[C@H:72]([C:78]([CH3:81])([CH3:80])[CH3:79])[NH:73][C:74]([O:76][CH3:77])=[O:75])[CH2:58][C@H:59]([OH:69])[C@@H:60]([NH2:68])[CH2:61][C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)=[CH:52][CH:51]=2)=[N:46]1)([CH3:44])([CH3:43])[CH3:42]>CN(C=O)C.C(Cl)Cl>[C:41]([N:45]1[N:49]=[N:48][C:47]([C:50]2[CH:55]=[CH:54][C:53]([CH2:56][N:57]([NH:70][C:71](=[O:82])[C@H:72]([C:78]([CH3:81])([CH3:80])[CH3:79])[NH:73][C:74]([O:76][CH3:77])=[O:75])[CH2:58][C@H:59]([OH:69])[C@@H:60]([NH:68][C:10](=[O:11])[C@H:6]([CH:7]([CH3:8])[CH3:9])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:61][C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)=[CH:52][CH:51]=2)=[N:46]1)([CH3:43])([CH3:42])[CH3:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 22940458HCID 22940458, compound

Product 1

HCID 467978
methyl N-[(1S)-1-[[(1S,2S)-1-benzyl-3-[[4-(2-tert-butyltetrazol-5-yl)phenyl]methyl-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethyl-butanoyl]amino]amino]-2-hydroxy-propyl]carbamoyl]-2-methyl-propyl]carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 54 mg (0.308 mmol) of N-methoxycarbonyl-(L)-valine and 92 mg (0.308 mmol) of TPTU in 1 ml of DMF and 101 μl (0.91 mmol) of NMM are stirred at room temperature for 10 min. 190 mg (0.308 mmol) of 1-[4-(2-tert-butyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-amino-2-N-[N-methoxycarbonyl-(L)-tert-leucyl]amino-6-phenyl-2-azahexane hydrochloride (Example 34g) in 2 ml of DMF are added thereto and the mixture is stirred at room temperature overnight to complete the reaction. The reaction mixture is diluted with methylene chloride and washed with brine. The aqueous phases are extracted 2× with methylene chloride; the organic phases are filtered through cotton wadding, concentrated by evaporation and chromatographed (SiO2; methylene chloride/methanol 30:1): TLC: Rf=0.21 (methylene chloride/methanol 19:1); FAB MS (M+H)+=738.

Workup

  1. customthe reaction
  2. washwashed with brine
  3. extractionThe aqueous phases are extracted 2× with methylene chloride
  4. filtrationthe organic phases are filtered through cotton wadding
  5. concentrationconcentrated by evaporation
  6. customchromatographed (SiO2; methylene chloride/methanol 30:1)

Sources & evidence

ORD record
ord-8f0939b356bd44ff94afa1370ce9fb59
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06300519B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes