Diethyl Ether → HCID 178482983, compound

HRID 1821455Notes

Reaction equation

C[NH:2]C1C=CC(C(N[C@@H](CCC(=O)NCCOCCOCCOCCOCCOCCNC(=O)COC2C=CC(C3NN=C4C5C=CC=C(NC(=O)NN6CCOCC6)C=5C(=O)C=34)=CC=2)C(OC(C)(C)C)=O)=[O:10])=CC=1.C(OCC)C.CO.C(Cl)Cl.[NH2:86][C:87]1[N:96]=[C:95]([NH2:97])[C:94]2[C:89](=[N:90][CH:91]=[C:92]([CH2:98][N:99]([CH3:173])[C:100]3[CH:105]=[CH:104][C:103]([C:106]([NH:108][C@@H:109]([CH2:117][CH2:118][C:119](=[O:172])[NH:120][CH2:121][CH2:122][O:123][CH2:124][CH2:125][O:126][CH2:127][CH2:128][O:129][CH2:130][CH2:131][O:132][CH2:133][CH2:134][O:135][CH2:136][CH2:137][NH:138][C:139](=[O:171])[CH2:140][O:141][C:142]4[CH:147]=[CH:146][C:145]([C:148]5[NH:152][N:151]=[C:150]6[C:153]7[CH:154]=[CH:155][CH:156]=[C:157]([NH:161][C:162]([NH:164][N:165]8[CH2:170][CH2:169][O:168][CH2:167][CH2:166]8)=[O:163])[C:158]=7[C:159](=[O:160])[C:149]=56)=[CH:144][CH:143]=4)[C:110]([O:112][C:113]([CH3:116])([CH3:115])[CH3:114])=[O:111])=[O:107])=[CH:102][CH:101]=3)[N:93]=2)[N:88]=1>CC(N(C)C)=O>[NH4+:2].[OH-:10].[NH2:86][C:87]1[N:96]=[C:95]([NH2:97])[C:94]2[C:89](=[N:90][CH:91]=[C:92]([CH2:98][N:99]([CH3:173])[C:100]3[CH:105]=[CH:104][C:103]([C:106]([NH:108][C@@H:109]([CH2:117][CH2:118][C:119](=[O:172])[NH:120][CH2:121][CH2:122][O:123][CH2:124][CH2:125][O:126][CH2:127][CH2:128][O:129][CH2:130][CH2:131][O:132][CH2:133][CH2:134][O:135][CH2:136][CH2:137][NH:138][C:139](=[O:171])[CH2:140][O:141][C:142]4[CH:143]=[CH:144][C:145]([C:148]5[NH:152][N:151]=[C:150]6[C:153]7[CH:154]=[CH:155][CH:156]=[C:157]([NH:161][C:162]([NH:164][N:165]8[CH2:170][CH2:169][O:168][CH2:167][CH2:166]8)=[O:163])[C:158]=7[C:159](=[O:160])[C:149]=56)=[CH:146][CH:147]=4)[C:110]([O:112][C:113]([CH3:114])([CH3:115])[CH3:116])=[O:111])=[O:107])=[CH:102][CH:101]=3)[N:93]=2)[N:88]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Compound 28 (0.65 g, 0.62 mmol) was dissolved in dimethylacetamide and 0,4 g of compound 14 (1.2 mmol) was added to the reaction mixture as a solid. The reaction mixture was heated to 60° C. for 6 hours, then let cool to room temperature and 80 ml diethyl ether added and let stand for 3 days. The supernantant was decanted off leaving a dark brown residue, which was purified by flash silica chromatography (5 to 10% MeOH/CH2Cl2 then 5 to 10% MeOH/CH2Cl2 W/1% NH4OH) to give 0.45 g (0.37 mmol, 60%) of a yellow solid (compound 30).

Workup

temperaturelet cool to room temperature
customThe supernantant was decanted off
customleaving a dark brown residue, which
customwas purified by flash silica chromatography (5 to 10% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-f8e5da0a416c4b3c95018df3dd912ba7
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605175B2

Reaction notes

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