Triethylamine → HCID 10457992, compound

HRID 265885Notes

Reaction equation

HRID 265885 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:54]1([S:60]([NH:63][C@@H:64]([CH2:68][NH2:69])[C:65]([OH:67])=[O:66])(=[O:62])=[O:61])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C=O)C>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:69][CH2:68][C@H:64]([NH:63][S:60]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)(=[O:62])=[O:61])[C:65]([OH:67])=[O:66])=[O:17])=[CH:18][CH:19]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10752796(2S)-3-amino-2-(benzenesulfonamido)propanoic AcidHCID 190341454-[3-(Pyridin-4-yl)propyloxy]benzoic acid

Product 1

HCID 10457992HCID 10457992, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 19-5 (200 mg, 0.78 mmol), NEt3 (0.22 mL, 1.5 mmol), and DMF (4 mL) at ambient temperature was treated with BOP (345 mg, 0.78 mmol). After 3.0 h, NEt3 (0.22 mL, 1.5 mmol) and 19-2 (190 mg, 0.78 mmol) were added. After 20 h, the reaction mixture was concentrated and subjected to flash chromatography (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH) to give impure 19-6 (400 mg). Prep HPLC purification (Delta Pak C-18Å column, 0 to 100% CH3CN/H2O containing 0.1% trifluoroacetic acid) gave pure 19-6 as a whim solid after lyophilization. Rf 0.74 (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH).

Workup

  1. waitAfter 20 h
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-9a3be4b102b74f0a80c4affd98609cfc
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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