Trifluoroacetic acid → D-Ornithyl-N-(Phenethyl)glycine 2-Naphthylamide Trifluoroacetate

HRID 1067080Notes

Reaction equation

HRID 1067080 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:45])[CH2:13][N:14]([C:23](=[O:44])[C@@H:24]([CH2:33][CH2:34][CH2:35][NH:36]C(OC(C)(C)C)=O)[NH:25]C(OC(C)(C)C)=O)[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:45])[CH2:13][N:14]([C:23](=[O:44])[C@@H:24]([CH2:33][CH2:34][CH2:35][NH2:36])[NH2:25])[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20662194Nalpha,Ndelta-Bis-Boc-D-ornithyl-N-(phenethyl)glycine 2-Naphthylamide

Product 1

HCID 70209615D-Ornithyl-N-(Phenethyl)glycine 2-Naphthylamide Trifluoroacetate

Procedure

A solution of Nα,Nδ-bis-Boc-D-ornithyl-N-(phenethyl)glycine 2-naphthylamide (100 mg) and trifluoroacetic acid (10 mL) was maintained at 25° C. for 1 hr, and then concentrated in vacuo. The residue was chromatographed on a reverse-phase column (Amberchrome) with elution with acetonitrile/0.1% aqueous trifluoroacetic acid. The appropriate fractions were lyophilized to afford the titled compound (45 mg):

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on a reverse-phase column (Amberchrome) with elution with acetonitrile/0.1% aqueous trifluoroacetic acid

Sources & evidence

ORD record
ord-992b78e0a3a94d4998f4df1848cf32a3
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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