Diethyl Ether → HCID 178448327, compound

HRID 362478Notes

Reaction equation

HRID 362478 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][C@H:21]([CH:34]=[O:35])[CH2:22][C:23](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[O:24]C(C)(C)C)=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12].C(Cl)Cl.C(O)(C(F)(F)F)=O.CCOCC>C1(OC)C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:18]([NH:20][C@H:21]([CH:34]=[O:35])[CH2:22][C:23](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[OH:24])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86583993HCID 86583993, compound

Product 1

HCID 178448327HCID 178448327, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

(3S)-3-[(1-Methylindole-2-carbonyl)valinyl]amino-4-oxobutanoic acid, t-butyl ester semicarbazone (170 mg, 0.36 mmol) was dissolved in anisole (0.2 mL) and methylene chloride (2 mL) and the resulting solution was treated with TFA (1 mL). The resulting solution was stirred for 3.5 hours under a nitrogen atmosphere at room temperature. The reaction mixture was concentrated in vacuo and chased with methylene chloride to give a purple foam. Trituration of the foam with ether afforded the title product as a solid purple powder (133 mg, 89%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and chased with methylene chloride
  2. customto give a purple foam

Sources & evidence

ORD record
ord-64f8bdf6174a4d0dbb811a57070325d7
Source dataset
uspto-grants-1999_02
Patent number
US05869519

Reaction notes

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