Diisopropylethylamine → HCID 58746524, compound
Reaction equation
[F:1][C:2]([F:7])([CH3:6])[C:3](O)=[O:4].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.FC(F)(F)C(O)=O.[NH2:42][C@@H:43]([CH2:64][C:65]1[CH:70]=[CH:69][C:68]([CH:71]2[S:75](=[O:77])(=[O:76])[NH:74][C:73](=[O:78])[CH2:72]2)=[C:67]([F:79])[CH:66]=1)[C:44]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:62]=[CH:61][CH:60]=[C:59]([OH:63])[C:54]=1[C:55]([O:57][CH3:58])=[O:56])=[O:45].C(N(CC)C(C)C)(C)C>CN(C=O)C>[F:1][C:2]([F:7])([CH3:6])[C:3]([NH:42][C@@H:43]([CH2:64][C:65]1[CH:70]=[CH:69][C:68]([CH:71]2[S:75](=[O:76])(=[O:77])[NH:74][C:73](=[O:78])[CH2:72]2)=[C:67]([F:79])[CH:66]=1)[C:44]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:62]=[CH:61][CH:60]=[C:59]([OH:63])[C:54]=1[C:55]([O:57][CH3:58])=[O:56])=[O:45])=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2,2-Difluoropropanoic acid (2.31 mg, 0.0210 mmol) in DMF (1.00 mL) was treated with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (9.97 mg, 0.0225 mmol). The solution was stirred at ambient temperature for 5 minutes. Methyl 2-[5-((2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorophenyl]-propanoylamino)pentyl]oxy-6-hydroxybenzoate trifluoroacetate (10.0 mg, 0.0150 mmol) in DMF (1.00 mL) was added followed by N,N-diisopropylethylamine (13.1 μL, 0.0751 mmol). The solution stirred at rt for 2 h. The product was directly purified by preparative LCMS to afford product as a white solid (7.1 mg, 73%). LCMS found for C28H33F3N3O9S (M+H)+: m/z=644.
Workup
- stirringThe solution stirred at rt for 2 h
- customThe product was directly purified by preparative LCMS
Sources & evidence
- ORD record
- ord-d21545721df444f2b7ca63fbc5349406
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141596B2
Reaction notes
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