Trifluoroacetic acid methylene chloride → HCID 59736809, compound

HRID 252873Notes

Reaction equation

HRID 252873 reaction equation
[C:1]([C:3]1[CH:42]=[CH:41][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[S:15][C:16]([C:19]([NH:21][C:22]4[CH:27]=[C:26]([C:28]5[S:29][CH:30]=[CH:31][CH:32]=5)[CH:25]=[CH:24][C:23]=4[NH:33]C(=O)OC(C)(C)C)=[O:20])=[CH:17][N:18]=3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].C(Cl)Cl.C(O)(C(F)(F)F)=O>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[S:15][C:16]([C:19]([NH:21][C:22]4[CH:27]=[C:26]([C:28]5[S:29][CH:30]=[CH:31][CH:32]=5)[CH:25]=[CH:24][C:23]=4[NH2:33])=[O:20])=[CH:17][N:18]=3)[CH2:10][CH2:9]2)=[CH:41][CH:42]=1)#[N:2]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 70336350HCID 70336350, compound

Product 1

HCID 59736809HCID 59736809, compoundYield 59%

Procedure

A solution of compound 340 (96 mg, 0.16 mmol) in 1:1 DCM/TFA (6 mL) was stirred at room temperature for 1 hour. The mixture was concentrated and purified by flash chromatography using EtOAc as an eluent, to afford the title compound 341 (47 mg, 59% yield). 1H NMR: (400.2 MHz, CD3OD) δ (ppm): 7.95 (br.s, 1H), 7.75 (m, 1H), 7.68 (m, 2H), 7.53 (t, 1H, J=7.6 Hz), 7.42 (s, 1H), 7.33 (d, 1H, J=8.2 Hz), 7.20 (m, 2H), 7.00 (m, 1H), 6.87 (d, 1H, J=8.3 Hz), 3.72 (s, 2H), 3.60 (m, 4H), 2.68 (m, 4H). MS: calc: 500.1; found: 501.2 (M+H)

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-965446a6f9c540a481cda37c2fe009db
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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