Triethylamine → HCID 86613021, compound

HRID 2263883Notes

Reaction equation

HRID 2263883 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:25]([C@@H:28]([CH2:46][C@H:47]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[C:54]([O:60][CH2:61][CH2:62][CH2:63][O:64][CH3:65])[CH:53]=1)[CH:48]([CH3:50])[CH3:49])[C@@H:29]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:30][C@@H:31]([CH:35]([CH3:37])[CH3:36])[C:32](O)=[O:33])=[N+:26]=[N-:27].[NH2:66][CH2:67][CH2:68][N:69]1[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1.CCN(CC)CC>CC#N.CCOC(C)=O>[N:69]1([CH2:68][CH2:67][NH:66][C:32](=[O:33])[C@H:31]([CH:35]([CH3:37])[CH3:36])[CH2:30][C@H:29]([O:38][Si:39]([C:42]([CH3:45])([CH3:43])[CH3:44])([CH3:40])[CH3:41])[C@@H:28]([N:25]=[N+:26]=[N-:27])[CH2:46][C@H:47]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[C:54]([O:60][CH2:61][CH2:62][CH2:63][O:64][CH3:65])[CH:53]=2)[CH:48]([CH3:49])[CH3:50])[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 33944N-(2-Aminoethyl)piperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57619557HCID 57619557, compound

Product 1

HCID 86613021HCID 86613021, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

HBTU (1.20 g, 3.0 mmol) was added to a solution of (2S,4S,5S,7S)-5-azido-4-(tert-butyl-dimethyl-silanyloxy)-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (1.50 g, 2.5 mmol) in CH3CN (50 mL). Then 2-aminoethylpiperidine (324 mg, 2.5 mmol) and NEt3 (3.9 mL) were added and the resulting solution was stirred at RT for 2.5 hours. For workup, EtOAc was added and the organic phase was washed with 1 N HCl, saturated NaHCO3 solution and brine. Drying of the organic phase (Na2SO4) and evaporation of the solvent affords the crude product which is purified by flash column chromatography [CH2Cl2:MeOH (95:5)] to give the desired product as a colorless oil. MS (LC-MS): 705.1 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 minutes, 100% CH3CN/3 minutes, 100-10% CH3CN/H2O/3 minutes, flow: 1.5 mL/min.): 6.82 minutes.

Workup

  1. washthe organic phase was washed with 1 N HCl, saturated NaHCO3 solution and brine
  2. dry with materialDrying of the organic phase (Na2SO4) and evaporation of the solvent
  3. customaffords the crude product which
  4. customis purified by flash column chromatography [CH2Cl2:MeOH (95:5)]

Sources & evidence

ORD record
ord-e35153a141cb42aeb10d84b158fd46e9
Source dataset
uspto-grants-2010_12
Patent number
US07851642B2

Reaction notes

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