Triethylamine → HCID 59843206, compound

HRID 2196529Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:32])[C:10]([NH:12][CH2:13][C:14]1[N:19]=[C:18]([N:20]2[C:24]([C:25]([OH:27])=O)=[CH:23][C:22]([C:28]([F:31])([F:30])[F:29])=[N:21]2)[CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:67][O:68][C:69]1[CH:76]=[CH:75][CH:74]=[CH:73][C:70]=1[CH2:71][NH2:72]>C(Cl)Cl>[CH3:67][O:68][C:69]1[CH:76]=[CH:75][CH:74]=[CH:73][C:70]=1[CH2:71][NH:72][C:25]([C:24]1[N:20]([C:18]2[N:19]=[C:14]([CH2:13][NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH3:32])[CH:15]=[CH:16][CH:17]=2)[N:21]=[C:22]([C:28]([F:31])([F:29])[F:30])[CH:23]=1)=[O:27]

Participants

Conditions

Temperature: 21 °C

Procedure

To a stirred solution of 49 (38 mg, 0.083 mmol) in CH2Cl2 (0.83 mL) were added triethylamine (0.025 mL, 0.183 mmol) and BOP (44.1 mg, 0.100 mmol) followed by 2-methoxybenzylamine (0.013 mL, 0.100 mmol). The resulting solution was allowed to stir at 21° C. overnight and evaporated to dryness. The residue was purified via ISCO flash chromatography (40% to 100% EtOAc/hexanes; 12G column). The title product 50 (28 mg, 59% yield) was isolated as a pale yellow oil. LRMS (ESI): calc. 576.6; found 577.6 (MH)+.

Workup

customevaporated to dryness
customThe residue was purified via ISCO flash chromatography (40% to 100% EtOAc/hexanes; 12G column)

Sources & evidence

ORD record: ord-be426b4d420c492fbef5218310bafaf9
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338437B2

Reaction notes

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