Trifluoroacetic acid → (2S)-6-[[(2S)-3-benzyloxy-2-(p-tolylsulfonylamino)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 396884Notes

Reaction equation

HRID 396884 reaction equation
[CH2:1]([N:5]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C@H:6]([C:29]([OH:31])=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH:2]([CH3:4])[CH3:3].C1C2C(COC([NH:59][C@H:60]([C:70]([OH:72])=O)[CH2:61][O:62][CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.C1CCC(N=C=N[CH:82]2[CH2:87][CH2:86][CH2:85][CH2:84][CH2:83]2)CC1.C1C=CC2N(O)N=NC=2C=1.CC1C=CC([S:105](Cl)(=[O:107])=[O:106])=CC=1.[C:109](O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:109][C:82]1[CH:83]=[CH:84][C:85]([S:105]([NH:59][C@H:60]([C:70]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([N:5]([S:32]([C:35]2[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=2)(=[O:33])=[O:34])[CH2:1][CH:2]([CH3:4])[CH3:3])[C:29]([OH:31])=[O:30])=[O:72])[CH2:61][O:62][CH2:63][C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)(=[O:107])=[O:106])=[CH:86][CH:87]=1

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 73974-Toluenesulfonyl chlorideHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3013742(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acidHCID 7017914Fmoc-O-benzyl-L-serine

Product 1

HCID 508563(2S)-6-[[(2S)-3-benzyloxy-2-(p-tolylsulfonylamino)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from solid phase bound Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine (200 mg, 0.1 mmol) in a similar fashion to general procedure Bb using commercially available Nα-(9-fluorenylmethoxycarbonyl)-O-benzyl-L-serine (100 mg, 0.24 mmol) with DCC (100 mg, 0.48 mmol) and HOBt (50 mg, 0.37 mmol) as the activating reagents. The intermediate adduct was again deprotected and coupled with 4-methylbenzenesulfonyl chloride in CH2Cl2 before being cleaved from the resin with TFA. The final product was purified by preparative HPLC to yield 30 mg (42%) of the desired material.

Workup

  1. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-271e8bc5ee4c42c19b6473b9de97a04a
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

Loading…