Trifluoroacetic acid → HCID 54254840, compound

HRID 849860Notes

Reaction equation

HRID 849860 reaction equation
[CH3:1][CH:2]([O:4][C:5]([C:7]1[N:11]=[C:10]([C@H:12]([N:24]([C:26](=[O:47])[C@H:27]([NH:39]C(OC(C)(C)C)=O)[CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[CH3:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[O:9][N:8]=1)=[O:6])[CH3:3].FC(F)(F)C(O)=O>ClCCl>[CH3:3][CH:2]([O:4][C:5]([C:7]1[N:11]=[C:10]([C@H:12]([N:24]([C:26](=[O:47])[C@H:27]([NH2:39])[CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[CH3:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[O:9][N:8]=1)=[O:6])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54169414HCID 54169414, compound

Product 1

HCID 54254840HCID 54254840, compoundYield 124.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-{(1R)-1-[N-((2R)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionyl)-N-methylamino]-2-(2-naphthyl)ethyl}-[1,2,4]oxadiazole-3-carboxylic acid (2-propyl)ester (2.1 g, 3.3 mmol) was suspended in a saturated mixture of trifluoroacetic acid and dichloromethane (1:1, 60 ml). After 10 min at 20° C., the reaction mixture was concentrated in vacuo to give 2.2 g of 5-{(1R)-1-[N-((2R)-2-amino-3-(2-naphthyl)propionyl)-N-methylamino]-2-(2-naphthyl)ethyl}-[1,2,4]oxadiazole-3-carboxylic acid (2-propyl)ester, trifluoroacetate, that was used for the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d0ea254fe20743e18fb602e23daabf56
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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