Benzylamine → HCID 57835543, compound

HRID 731163Notes

Reaction equation

HRID 731163 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([NH:32][C@@H:33]([CH2:51][C@H:52]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[C:59]([O:65][CH2:66][CH2:67][CH2:68][O:69][CH3:70])[CH:58]=1)[CH:53]([CH3:55])[CH3:54])[C@@H:34]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[CH2:35][C@@H:36]([CH:40]([CH3:42])[CH3:41])[C:37](O)=[O:38])=[O:31])([CH3:28])([CH3:27])[CH3:26].[CH2:71]([NH2:78])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1.CCOC(C)=O>C(#N)C.CN(C=O)C>[C:25]([O:29][C:30](=[O:31])[NH:32][C@@H:33]([CH2:51][C@H:52]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[C:59]([O:65][CH2:66][CH2:67][CH2:68][O:69][CH3:70])[CH:58]=1)[CH:53]([CH3:54])[CH3:55])[C@@H:34]([O:43][Si:44]([C:47]([CH3:48])([CH3:50])[CH3:49])([CH3:45])[CH3:46])[CH2:35][C@H:36]([C:37](=[O:38])[NH:78][CH2:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)[CH:40]([CH3:41])[CH3:42])([CH3:26])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57835530HCID 57835530, compound

Product 1

HCID 57835543HCID 57835543, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

HBTU (400 mg, 1.03 mmol, 1.2 equiv.) is added to a solution of (2S,4S,5S,7S)-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (575 mg, 0.86 mmol, 1.0 equiv.) in acetonitrile (CH3CN) (15 mL) and DMF (1 mL) at 0° C. After 5 minutes, a solution of benzylamine (94 μL, 0.86 mmol, 1.0 equiv.) and Net3 (1.2 mL, 8.6 mmol, 10 equiv.) in CH3CN (3 mL) is added and the reaction mixture is stirred at room temperature for 5 minutes. For workup EtOAc is added and the organic layer is washed with 1 N HCl, a saturated solution of sodium bicarbonate (NaHCO3) and brine. Drying (Na2SO4) of the organic phase and evaporation of the solvent affords the crude product which is purified by flash column chromatography [50 g SiO2, hexane:EtOAc (4:1)] to afford the desired product as a colorless foam. MS (LC-MS): 780.4 [M+Na]+; Rf [hexane:EtOAc (1:1)]: 0.65 minutes.

Workup

  1. washthe organic layer is washed with 1 N HCl
  2. customDrying
  3. custom(Na2SO4) of the organic phase and evaporation of the solvent
  4. customaffords the crude product which
  5. customis purified by flash column chromatography [50 g SiO2, hexane:EtOAc (4:1)]

Sources & evidence

ORD record
ord-bb8ae125618240309baa493918b1952d
Source dataset
uspto-grants-2009_09
Patent number
US07582782B2

Reaction notes

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