Benzenepentanoic acid → L-Alanine

HRID 2288057Notes

Reaction equation

HRID 2288057 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:34](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:35]([C:37]([OH:39])=[O:38])[CH3:36].[NH:57](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:58]([C:83]([OH:85])=[O:84])[CH2:59][CH2:60][CH2:61][NH:62][C:63](=[NH:82])[NH:64]S(C1C(C)=C2C(OC(C2)(C)C)=C(C)C=1C)(=O)=O.C1(CCCCC(O)=O)C=CC=CC=1>>[NH2:34][C@H:35]([C:37]([OH:39])=[O:38])[CH3:36].[NH2:57][C@H:58]([C:83]([OH:85])=[O:84])[CH2:59][CH2:60][CH2:61][NH:62][C:63](=[NH:64])[NH2:82]

Participants

6

Reactant 4

HCID 16757Benzenepentanoic acidHCID 6364642N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanineHCID 86609734Hbtu dipeaHCID 178427572HCID 178427572, compound

Product 2

HCID 5950L-AlanineHCID 178418600HCID 178418600, compound

Procedure

An analogous procedure to that described in Example 2.6 was used, except that the whole of the peptide assembly was performed manually using HBTU/DIPEA activation, coupling Fmoc-Papa-OH, Fmoc-Ala-OH, Fmoc-Arg(Pbf)-OH, Fmoc-IIb-OH and 5-phenylvaleric acid in the appropriate order. The peptide was cleaved from the resin using a similar procedure to that described in Example 2.6. The product was purified using preparative RP-HPLC in a similar manner to that described for Example 1.4, eluting with a gradient of acetonitrile-water containing 0.1% TFA (15-30% acetonitrile) over 90 minutes at a flow rate of 10 ml/minute. The product was characterised by HPLC, mass spectroscopy and amino acid analysis in a similar manner to that described for Example 1.4; RP-HPLC (eluting with acetonitrile and water containing 0.1% TFA, using a 15-30% acetonitrile gradient over 30 minutes, flow rate 1.0 ml/minute) retention time=20.02 minutes; mass spectrometry, m/e (ES+) 1061.6 (MH+), 531.4 (M+2H++); amino acid analysis gave Ala 4.16, Arg 2.00, IIb present.

Workup

  1. customThe product was purified
  2. washeluting with a gradient of acetonitrile-water containing 0.1% TFA (15-30% acetonitrile) over 90 minutes at a flow rate of 10 ml/minute
  3. washRP-HPLC (eluting with acetonitrile and water containing 0.1% TFA

Sources & evidence

ORD record
ord-3ad46da9cef047b0ab604da1bfa0a706
Source dataset
uspto-grants-2000_07
Patent number
US06087336

Reaction notes

Loading…