Trifluoroacetate → HCID 178446000, compound

HRID 1380447Notes

Reaction equation

HRID 1380447 reaction equation
FC(F)(F)C([O-])=O.[NH2:8][C@H:9]([C:20]([NH:22][C@H:23]([C:28]([NH2:30])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:19])[NH:15][N+:16]([O-:18])=[O:17].[NH:31](C(OC(C)(C)C)=O)[C@H:32]([C:34](O)=[O:35])[CH3:33].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[NH2:31][C@H:32]([C:34]([NH:8][C@H:9]([C:20]([NH:22][C@H:23]([C:28]([NH2:30])=[O:29])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:21])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:19])[NH:15][N+:16]([O-:18])=[O:17])=[O:35])[CH3:33]

Participants

6

Reactant 4

HCID 84468TrifluoroacetateHCID 85082Tert-butoxycarbonylalanineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178446021H-Arg(NO2)Leu-NH2

Product 1

HCID 178446000HCID 178446000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

443 g of trifluoroacetate of H-Arg(NO2)Leu-NH2 are dissolved in 2 l of DMF. 200 g of Boc-Ala-OH, then 500 g of BOP are added. The pH is adjusted to 7 with pH paper (on small samples of the reaction medium) with the aid of NEM. The medium is stirred and the development of the reaction is followed by TLC. The reaction is terminated after 4 hrs. The medium is evaporated to dryness in vacuo at 25°. The residue is taken up in 2 l of water and 2 l of ethyl acetate. The organic phase is washed with a 5% aqueous solution of NaHCO3, with water, dried and evaporated. The tripeptide is recrystallized in ethyl-acetate/ether, and finally dried in vacuo. It is monitored by TLC and NMR.

Workup

  1. customThe reaction is terminated after 4 hrs
  2. customThe medium is evaporated to dryness in vacuo at 25°
  3. washThe organic phase is washed with a 5% aqueous solution of NaHCO3, with water
  4. customdried
  5. customevaporated
  6. customThe tripeptide is recrystallized in ethyl-acetate/ether
  7. customfinally dried in vacuo

Sources & evidence

ORD record
ord-02da381ad6f44ac1921a26faa9b4874e
Source dataset
uspto-grants-1986_04
Patent number
US04581168

Reaction notes

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