Hydrochloric Acid → HCID 86681377, compound

HRID 1406680Notes

Reaction equation

HRID 1406680 reaction equation
[C:1]1([C:7]2([C:12]3[CH:29]=[CH:28][C:15]([CH2:16][N:17]4[CH2:22][CH2:21][N:20]([CH2:23][C:24]([NH:26][NH2:27])=[O:25])[CH2:19][CH2:18]4)=[CH:14][CH:13]=3)OCC[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CO>[C:7]([C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[CH2:18][CH2:19][N:20]([CH2:23][C:24]([NH:26][NH2:27])=[O:25])[CH2:21][CH2:22]2)=[CH:28][CH:29]=1)(=[O:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86681376HCID 86681376, compound

Product 1

HCID 86681377HCID 86681377, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 15 (1.82 g, 4.57 mmol, 1.0 equiv.) in MeOH (14 mL, 0.33 M) was added 10% aqueous HCl (14 mL). The reaction mixture was stirred overnight at room temperature. The MeOH was evaporated, and the resulting aqueous solution was made basic (pH>12) by the addition of 1M NaOH. The aqueous solution was extracted with DCM (4×25 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4, filtered, and concentrated to yield 1{31} (726 mg, 45%) as a yellow oily solid, which was used without further purification. 1H-NMR (500 MHz, CDCl3): δ 8.16 (br s, 1H), 7.75-7.71 (m, 4H), 7.53 (t, 1H, J=7.5 Hz), 7.42 (t, 2H, J=7.5 Hz), 7.38 (d, 2H, J=8.0 Hz), 3.85 (br s, 2H), 3.53 (s, 2H), 3.03 (s, 2H), 2.51 (br s, 4H), 2.45 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 196.2, 170.2, 142.9, 137.4, 136.2, 132.2, 130.0, 129.8, 128.6, 128.1, 62.2, 60.4, 53.4, 52.9.

Workup

  1. customThe MeOH was evaporated
  2. additionby the addition of 1M NaOH
  3. extractionThe aqueous solution was extracted with DCM (4×25 mL)
  4. washThe combined organic layers were washed with brine (25 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1c61bce1efa24971b11141c790f3cd03
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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