Dichloromethane ethylacetate → HCID 135445666, compound

HRID 1967221Notes

Reaction equation

HRID 1967221 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]([CH:37]5OCC(C)(C)C[O:38]5)=[C:20]5[NH:36][C:23](=[C:24]([C:30]6[CH:35]=[CH:34][CH:33]=[CH:32][CH: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.C(OCC)(=O)C>C(Cl)Cl>[CH:5]([C:8]1[C:9]2[NH:13][C:12]([C:14]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)=[C:15]3[N:45]=[C:18]([C:19]([CH:37]=[O:38])=[C:20]4[NH:36][C:23](=[C:24]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[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

5

Reactant 3

HCID 21226138Dichloromethane ethylacetateHCID 22392675Trifluoroacetic acid waterHCID 178428914HCID 178428914, compound

Product 1

HCID 135445666HCID 135445666, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As described for 5, a solution of 14 (30 mg, 44 μmol) in CH2Cl2 (5.0 mL) was treated with TFA/water (2.0 mL, 1:1) with stirring at room temperature for 3 days. Standard workup including chromatography (silica, CH2Cl2/ethyl acetate) gave a purple green solid (18.7 mg, 83%): IR (neat) 1673, 1550, 1120 cm−1; 1H NMR δ−2.30 (s, 2H), 7.80-7.82 (m, 6H), 8.17-8.19 (m, 4H), 8.59 (d, J=4.8 Hz, 4H), 10.02 (s, 4H), 12.55 (s, 2H); LD-MS obsd 518.90, calcd 518.1743 (C34H22N4O2); λabs 428, 538, 584, 622, 684 nm.

Sources & evidence

ORD record
ord-9766bd08517f4a8fb83b1c4e1d94e3a4
Source dataset
uspto-grants-2013_04
Patent number
US08420804B2

Reaction notes

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