HCID 15983581, compound → HCID 46916884, compound

HRID 2358928Notes

Reaction equation

HRID 2358928 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:11][C:12]([C:14]23[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:22][C:16]([C:24]5[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=5)([CH2:17]4)[CH2:15]2)[CH2:21]3)=[O:13])[CH:5]=[CH:6][C:7]=1[OH:8]>C(OC(=O)C(C)C)(=O)C(C)C.OS(O)(=O)=O>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([C:16]23[CH2:17][CH:18]4[CH2:19][CH:20]([CH2:21][C:14]([C:12]([NH:11][CH2:10][CH2:9][C:4]5[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([O:1][C:12](=[O:13])[CH:14]([CH3:21])[CH3:15])[CH:3]=5)=[O:13])([CH2:23]4)[CH2:15]2)[CH2:22]3)=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 15983581HCID 15983581, compound

Product 1

HCID 46916884HCID 46916884, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 7346Isobutyric anhydrideSolvent

Procedure

Compound 1 was dissolved in iso-butyric anhydride with a catalytic amount of 98% H2SO4 and stirred under N2 for 3 days at room temperature. The solution was then concentrated under a vacuum and filtered to give the product Compound 5, with a melting point of 126-128° C. 1H NMR (500 MHz, CDCl3) δ 1.29-1.33 (d, d, 6H, 2CH3), 1.74 (m, 2H, Admant-H), 1.81-1.88 (m, 8H, Admant-H), 1.94 (s, 2H, Admant-H), 2.26 (m, 2H, Admant-H), 2.74-2.81 (m, 2H, 2COCH), 2.82-2.85 (t, J=7.5 Hz, 2H, CH2), 3.50-3.54 (q, 2H, NCH2), 5.68 (s, 1H, NH), 6.99 (s, 1H, Ar—H), 7.05-7.07 (d, d, 1H, H—Ar), 7.11-7.13 (d, J=10 Hz, 1H, Ar—H), 7.30 (s, 4H, Ar—H); 13C NMR (500 MHz, CDCl3) δ 18.9, 28.8, 34.0, 35.0, 35.5, 36.5, 38.3, 40.3, 41.7, 42.0, 44.4, 123.5, 123.9, 126.4, 126.7, 128.3, 131.5, 137.7, 140.9, 142.2, 148.4, 174.4, 174.5, 177.4; MS m/z (relative intensity) 566.22 (MH+, 50), 567.22 (10), 567.22 (15).

Workup

  1. concentrationThe solution was then concentrated under a vacuum
  2. filtrationfiltered

Sources & evidence

ORD record
ord-03281f1d0d0d4dd3a2c2876651e5d3af
Source dataset
uspto-grants-2014_04
Patent number
US08685936B2

Reaction notes

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