Trifluoroacetic acid → HCID 178446022, compound

HRID 1371286Notes

Reaction equation

HRID 1371286 reaction equation
C([O:5][C:6](=[N:34][NH:35][C:36]([NH2:38])=[O:37])[CH2:7][C@H:8]([NH:11][C:12](=[O:33])[C@H:13]([CH2:29][CH:30]([CH3:32])[CH3:31])[NH:14][C:15](=[O:28])[CH2:16][NH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[CH:9]=[O:10])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:18]1([NH:17][CH2:16][C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:8]([CH:9]=[O:10])[CH2:7][C:6](=[N:34][NH:35][C:36]([NH2:38])=[O:37])[OH:5])=[O:33])[CH2:29][CH:30]([CH3:32])[CH3:31])=[O:28])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86585452(3S)-3-[N-((1-Naphthylamino)Acetyl)Leucinyl]Amino-4-Oxobutanoic Acid tert-Butyl Ester Semicarbazone

Product 1

HCID 178446022HCID 178446022, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S)-3-[N-((1-naphthylamino)acetyl)leucinyl]amino-4-oxobutanoic acid tert-butyl ester semicarbazone (0.201 g, 0.38 mmol) in CH2Cl2(2.0 mL)-anisole(0.5 mL) at room temperature under nitrogen was added trifluoroacetic acid (2.0 mL). The resulting solution was stirred at room temperature for 5 hrs, evaporated to dryness and chased with CH2Cl2 and toluene-CH2Cl2 (1:1). The resulting solid was triturated with CHCl2-Et2O to give the title compound (0.176 g, 98%) as a pale gray solid. TLC(EtOAc-pyridine-AcOH-H2O; 60:20:5:10) Rf=0.45.

Workup

  1. customevaporated to dryness and chased with CH2Cl2 and toluene-CH2Cl2 (1:1)
  2. customThe resulting solid was triturated with CHCl2-Et2O

Sources & evidence

ORD record
ord-0099f33ab37849df843532d42cabbbbe
Source dataset
uspto-grants-2007_01
Patent number
US07157430B2

Reaction notes

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