Trifluoroacetate → HCID 178462179, compound

HRID 246913Notes

Reaction equation

HRID 246913 reaction equation
FC(F)(F)C([O-])=O.[NH2:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:16])[NH2:15].[NH:20](C(OC(C)(C)C)=O)[C@H:21]([C:23](O)=[O:24])[CH3:22].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>[NH2:20][C@H:21]([C:23]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:15])[NH2:16])=[O:24])[CH3:22]

Participants

6

Reactant 4

HCID 84468TrifluoroacetateHCID 85082Tert-butoxycarbonylalanineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178418600HCID 178418600, compound

Product 1

HCID 178462179HCID 178462179, 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-be3c7ea898e04beda97c7de9a7faf593
Source dataset
uspto-grants-1987_11
Patent number
US04704450

Reaction notes

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