Trifluoroacetic acid → HCID 178427179, compound

HRID 2053930Notes

Reaction equation

HRID 2053930 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[N:10]=[C:9]1[C@@H:18]([NH:24][C:25](=[O:40])[C:26]1[CH:31]=[CH:30][C:29]([C:32]([N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:33])=[C:28]([CH3:39])[CH:27]=1)[CH2:19][CH2:20][C:21](O)=[O:22])=O)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH:72]1[CH2:76][CH2:75][C@H:74]([OH:77])[CH2:73]1.FC(F)(F)C(O)=O.ClCl>C(#N)C.C(OCC)(=O)C.C(O)C>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]2[NH:8][C:9]([C@@H:18]([NH:24][C:25](=[O:40])[C:26]3[CH:31]=[CH:30][C:29]([C:32]([N:34]4[CH2:35][CH2:36][CH2:37][CH2:38]4)=[O:33])=[C:28]([CH3:39])[CH:27]=3)[CH2:19][CH2:20][C:21]([N:72]3[CH2:76][CH2:75][C@H:74]([OH:77])[CH2:73]3)=[O:22])=[N:10][C:11]=2[CH:16]=1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733874(3S)-pyrrolidin-3-olHCID 69309945HCID 69309945, compound

Product 1

HCID 178427179HCID 178427179, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

Prepared analogously to Example 1g from (S)—N-[1-(1-tert-butoxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonylpropyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, TBTU, diisopropylethylamine, (S)pyrrolidine-3-ol in acetonitrile, and subsequent reaction with trifluoroacetic acid analogously to Example 17. Yield: 87%; Rf value: 0.18 (silica gel; ethyl acetate/ethanol=85:15); C28H32ClN5O4 (538.05); mass spectrum: (M+H)+=538/540 (chlorine isotope).

Sources & evidence

ORD record
ord-92376e9d4cae4562b6a8ac5192420300
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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