Trifluoroacetate → HCID 178445999, compound

HRID 1380449Notes

Reaction equation

HRID 1380449 reaction equation
FC(F)(F)C([O-])=O.N(C(OCC1C=CC=CC=1)=O)[C@H](C(O)=O)C.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(O)(C(F)(F)F)=O.C(Cl)Cl.[NH:61]([C:108]([O:110][CH2:111][C:112]1[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=1)=[O:109])[C@H:62]([C:64]([NH:66][C@H:67]([C:78]([NH:80][C@H:81]([C:83]([NH:85][C@H:86]([C:97]([NH:99][C@H:100]([C:105]([NH2:107])=[O:106])[CH2:101][CH:102]([CH3:104])[CH3:103])=[O:98])[CH2:87][CH2:88][CH2:89][NH:90][C:91](=[NH:96])[NH:92][N+]([O-])=O)=[O:84])[CH3:82])=[O:79])[CH2:68][CH2:69][CH2:70][NH:71][C:72](=[NH:77])[NH:73][N+:74]([O-:76])=[O:75])=[O:65])[CH3:63]>CN(C=O)C>[NH:61]([C:108]([O:110][CH2:111][C:112]1[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=1)=[O:109])[C@H:62]([C:64]([NH:66][C@H:67]([C:78]([NH:80][C@H:81]([C:83]([NH:85][C@H:86]([C:97]([NH:99][C@H:100]([C:105]([NH2:107])=[O:106])[CH2:101][CH:102]([CH3:104])[CH3:103])=[O:98])[CH2:87][CH2:88][CH2:89][NH:90][C:91](=[NH:92])[NH2:96])=[O:84])[CH3:82])=[O:79])[CH2:68][CH2:69][CH2:70][NH:71][C:72](=[NH:77])[NH:73][N+:74]([O-:76])=[O:75])=[O:65])[CH3:63]

Participants

7

Reactant 5

HCID 84468TrifluoroacetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 736104N-carbobenzyloxyalanineHCID 21863450Trifluoroacetic acid methylene chlorideHCID 178446001HCID 178446001, compound

Product 1

HCID 178445999HCID 178445999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

From 715 g of trifluoroacetate of E-Arg(NO2)Ala-Arg(NO2)-Leu-NH2 in solution in 4 l of DMF and 233 g of Z-Ala-OH and 500 g of BOP employing the same technique as the one described in I-2 (and without treatment in that case by TFA-CH2Cl2), 612 g of Z-Ala-Arg(NO2)-Ala-Arg(NO2)Leu-NH2 (76%) are obtained, after recrystallization in the DMF-ether mixture, in the form of a white pulverulent solid, monitored by TLC and NMR.

Workup

  1. customare obtained
  2. customafter recrystallization in the DMF-ether mixture

Sources & evidence

ORD record
ord-65781a2b79914a85afb12fbc1a41683b
Source dataset
uspto-grants-1986_04
Patent number
US04581168

Reaction notes

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