Trifluoroacetic acid water → HCID 135445249, compound

HRID 1784131Notes

Reaction equation

HRID 1784131 reaction equation
CC1(C)CO[CH:5]([C:8]2[C:9]3[NH:13][C:12]([C:14]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[C:15]4[N:45]=[C:18]([C:19]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)=[C:20]5[NH:38][C:23](=[C:24]([CH:30]6OCC(C)(C)C[O:31]6)[C:25]6[CH:26]=[CH:27][C:28]=2[N:29]=6)[CH:22]=[CH:21]5)[CH:17]=[CH:16]4)=[CH:11][CH:10]=3)[O:4]C1.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[CH:5]([C:8]1[C:9]2[NH:13][C:12]([C:14]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[C:15]3[N:45]=[C:18]([C:19]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)=[C:20]4[NH:38][C:23](=[C:24]([CH:30]=[O:31])[C:25]5[CH:26]=[CH:27][C:28]=1[N:29]=5)[CH:22]=[CH:21]4)[CH:17]=[CH:16]3)=[CH:11][CH:10]=2)=[O:4]

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 173045429HCID 173045429, compound

Product 1

HCID 135445249HCID 135445249, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As described for 5, a solution of 17 (30 mg, 44 μmol) in CH2Cl2 (5.0 mL) was treated with TFA/water (2.0 mL, 1:1) at room temperature for 3 days. The standard workup including chromatography (silica, CHCl3/hexanes) afforded a purple solid (19.8 mg, 88%): IR (neat) 1672, 1548, 1166 cm−1; 1H NMR δ −2.19 (s, 2H), 7.76-7.83 (m, 6H), 8.15-8.17 (m, 4H), 8.66 (s, 2H), 8.93 (d, J=4.8 Hz, 2H), 9.79 (s, 2H), 9.89 (s, 2H), 12.28 (s, 2H); 13C NMR δ 194.8, 141.0, 134.5, 128.7, 127.2, 109.7, 100.1; LD-MS obsd 519.18; FAB-MS obsd 519.1839, calcd 519.1821 (C34H22N4O2); λabs 440, 535, 607, 655 nm.

Sources & evidence

ORD record
ord-0986f615c1f044319bcf86fa07aa69f1
Source dataset
uspto-grants-2009_03
Patent number
US07501507B2

Reaction notes

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