HCID 15983581, compound → HCID 46916882, compound

HRID 2358927Notes

Reaction equation

HRID 2358927 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)CCC)(=O)CCC.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][CH2:15][CH3:16])(=[O:1])[CH2:7][CH2:6][CH3:5]

Participants

4

Reactant 1

HCID 15983581HCID 15983581, compound

Product 1

HCID 46916882HCID 46916882, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 7798Butyric anhydrideSolvent

Procedure

Compound 1 was dissolved in n-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 4, with a melting point of 78-80° C. 1H NMR (500 MHz, CDCl3) δ 1.03-1.08 (m, 6H, 2CH3), 1.74 (m, 2H, Admant-H), 1.75-1.87 (m, 12H, 2CH2, Admant-H), 1.93 (s, 2H, Admant-H), 2.26 (m, 2H, Admant-H), 2.49-2.55 (m, 4H, 2COCH2), 2.82-2.85 (t, J=7.5 Hz, 2H, CH2), 3.50-3.54 (q, 2H, NCH2), 5.69 (s, 1H, NH), 7.01-7.02 (d, J=5 Hz, 1H, Ar—H), 7.06-7.08 (d, d, 1H, H—Ar), 7.12-7.14 (d, J=10 Hz, 1H, Ar—H), 7.30 (s, 4H, Ar—H); MS m/z (relative intensity) 566.73 (MH+, 50), 567.61 (12), 568.60 (20).

Workup

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

Sources & evidence

ORD record
ord-1e3300d867b84a109c94a32775139f8a
Source dataset
uspto-grants-2014_04
Patent number
US08685936B2

Reaction notes

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