HCID 15983581, compound → HCID 46916883, compound

HRID 2358926Notes

Reaction equation

HRID 2358926 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)CC)(=O)CC.OS(O)(=O)=O>[C:2]([O:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][CH2:10][NH:11][C:12]([C:14]23[CH2:21][CH:20]4[CH2:19][CH:18]([CH2:17][C:16]([C:24]5[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=5)([CH2:22]4)[CH2:15]2)[CH2:23]3)=[O:13])=[CH:3][C:2]=1[O:1][C:12](=[O:13])[CH2:14][CH3:15])(=[O:1])[CH2:7][CH3:6]

Participants

4

Reactant 1

HCID 15983581HCID 15983581, compound

Product 1

HCID 46916883HCID 46916883, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 31263Propionic anhydrideSolvent

Procedure

Compound 1 was dissolved in propionic 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 3, with a melting point of 114-115° C. 1H NMR (500 MHz, CDCl3) δ 1.24-1.30 (m, 6H, 2CH3), 1.74 (m, 2H, Admant-H), 1.84-1.87 (m, 8H, Admant-H), 1.93 (s, 2H, Admant-H), 2.26 (m, 2H, Admant-H), 2.53-2.61 (m, 4H, 2COCH2), 2.82-2.85 (t, J=7.5 Hz, 2H, CH2), 3.50-3.54 (q, 2H, NCH2), 5.40 (s, 1H, NH), 7.01-7.02 (d, J=5 Hz, 1H, Ar—H), 7.06-7.08 (d, d, 1H, H—Ar), 7.13-7.15 (d, J=10 Hz, 1H, Ar—H), 7.30 (s, 4H, Ar—H); 13C NMR (500 MHz, CDCl3) δ 9.1, 27.5, 28.8, 35.0, 35.5, 36.5, 38.3, 40.3, 41.7, 42.0, 44.5, 123.5, 123.9, 126.4, 126.8, 128.3, 131.5, 137.8, 140.7, 142.1, 148.4, 171.7, 171.8, 177.4; MS m/z (relative intensity) 538.61 (MH+, 100), 539.61 (38), 540.61 (45).

Workup

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

Sources & evidence

ORD record
ord-b9fca7f848b74c6c8da0e271102ba9ba
Source dataset
uspto-grants-2014_04
Patent number
US08685936B2

Reaction notes

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