Acetic Acid → HCID 91446597, compound

HRID 272741Notes

Reaction equation

HRID 272741 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:15]=[CH:16][C:17]4[C:23](=[O:24])[NH:22][C:21]5[CH:25]=[C:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:28][C:20]=5[NH:19][C:18]=4[CH:34]=3)=[CH:10][C:9]=2[O:35][CH3:36])=[CH:4][CH:3]=1.C(O)(=[O:39])C>O.C(OCC)(=O)C>[CH3:36][O:35][C:9]1[CH:10]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]3[C:23](=[O:24])[NH:22][C:21]4[CH:25]=[C:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:28][C:20]=4[NH:19][C:18]=3[CH:34]=2)[CH:12]=[CH:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2](=[O:39])[NH:7][CH:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 91523691HCID 91523691, compound

Product 1

HCID 91446597HCID 91446597, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 656A (20 mg, 0.04 mmol) in acetic acid (1 mL) and water (200 μL) was heated at 100° C. overnight, cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by preparative HPLC (2.5 mg, 13% yield). MS (ESI) m/e 482 (M+H)+; 1H NMR (400 MHz, DMSO-d.6 □ 11.67 (br s, 1H), 9.83 (s, 1H), 7.95 (s, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.69 (dd, J=9.7, 2.5 Hz, 1H), 7.56 (m, 1H), 7.24-7.43 (m, 5H), 6.96 (d, J=8.1 Hz, 1H), 6.82-6.87 (m, 2H), 6.39 (d, J=9.2 Hz, 1H), 3.90 (s, 3H), 3.60 (s, 3H), 3.54 (s, 2H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by preparative HPLC (2.5 mg, 13% yield)

Sources & evidence

ORD record
ord-fe126762862e4227862345bda9d7eed7
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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