Trifluoroacetate → HCID 178445999, compound

HRID 2291755Notes

Reaction equation

HRID 2291755 reaction equation
FC(F)(F)[C:3]([O-:5])=[O:4].[NH2:8][C@H:9]([C:20]([NH:22][C@H:23]([C:25]([NH:27][C@H:28]([C:39]([NH:41][C@H:42]([C:47]([NH2:49])=[O:48])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:40])[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[NH:38])[NH:34][N+]([O-])=O)=[O:26])[CH3:24])=[O:21])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:19])[NH:15][N+:16]([O-:18])=[O:17].N(C(O[CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=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:103](C(OCC1C=CC=CC=1)=O)[C@H:104]([C:106](N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N)=O)CC(C)C)=O)CCCNC(=N)N[N+]([O-])=O)=O)C)=O)CCCNC(=N)N[N+]([O-])=O)=[O:107])[CH3:105]>CN(C=O)C>[NH:103]([C:3]([O:5][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:4])[C@H:104]([C:106]([NH:8][C@H:9]([C:20]([NH:22][C@H:23]([C:25]([NH:27][C@H:28]([C:39]([NH:41][C@H:42]([C:47]([NH2:49])=[O:48])[CH2:43][CH:44]([CH3:45])[CH3:46])=[O:40])[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[NH:38])[NH2:34])=[O:26])[CH3:24])=[O:21])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:19])[NH:15][N+:16]([O-:18])=[O:17])=[O:107])[CH3:105]

Participants

8

Reactant 6

HCID 84468TrifluoroacetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 736104N-carbobenzyloxyalanineHCID 21863450Trifluoroacetic acid methylene chlorideHCID 178446001HCID 178446001, compoundHCID 178446002HCID 178446002, compound

Product 1

HCID 178445999HCID 178445999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

From 715 g of trifluoroacetate of H-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-51950624b03246dcb0aa09dbf67d136b
Source dataset
uspto-grants-1989_01
Patent number
US04797469

Reaction notes

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