Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 178468071, compound

HRID 1828102Notes

Reaction equation

HRID 1828102 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:28]([O:30][CH:31]([C:45]([O:47]CC)=O)[NH:32][C:33](=[O:44])[C:34]1[C:35](=[C:39]([F:43])[CH:40]=[CH:41][CH:42]=1)[C:36]([OH:38])=O)[CH3:29].C(OC(C(OCC)=O)NC(=O)C1C(=CC=CC=1F)C(O)=O)C.[CH2:72]([O:79][C:80](=[O:92])/[N:81]=[C:82](\[NH2:91])/[C:83]1[CH:88]=[CH:87][C:86]([CH2:89][NH2:90])=[CH:85][CH:84]=1)[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1>>[CH2:72]([O:79][C:80](=[O:92])/[N:81]=[C:82](\[NH2:91])/[C:83]1[CH:84]=[CH:85][C:86]([CH2:89][NH:90][C:45](=[O:47])[CH:31]([O:30][CH2:28][CH3:29])[N:32]2[C:36](=[O:38])[C:35]3[C:34](=[CH:42][CH:41]=[CH:40][C:39]=3[F:43])[C:33]2=[O:44])=[CH:87][CH:88]=1)[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1

Participants

5

Reactant 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11121820HCID 11121820, compoundHCID 22064636HCID 22064636, compoundHCID 22064681HCID 22064681, compound

Product 1

HCID 178468071HCID 178468071, compound

Procedure

According to general procedure C, but using 2.2 eq. of BOP coupling reagent and adding the amine component after a delay time of 1 h, (RS)-N-(ethoxy-ethoxycarbonyl-methyl)-6-fluoro-phthalamic acid and its regioisomer (RS)-N-(ethoxy-ethoxycarbonyl-methyl)-3-fluoro-phthalamic acid was reacted with [1-amino-1-(4-aminomethyl-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester to give (RS)-[1-amino-1-(4-{[2-ethoxy-2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester, MS 533.4 ([M+H]+).

Sources & evidence

ORD record
ord-08f00e1cb8064226b404d576a600e886
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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