Hydrochloric Acid → HCID 57611913, compound

HRID 1919879Notes

Reaction equation

HRID 1919879 reaction equation
[NH2:1][CH:2]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(C(C)C)C(C)C.[C:26](OC(=O)C)(=[O:28])[CH3:27].Cl>C1COCC1>[C:26]([NH:1][CH:2]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 57611946HCID 57611946, compound

Product 1

HCID 57611913HCID 57611913, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-amino-2-ethoxy-2-oxoethyl)benzoic acid, as described in Example 1, Step B, (0.94 g, 2.79 mmol) and DIPEA (1.509 mL, 8.64 mmol) were suspended in THF (4 mL) and acetic anhydride (0.289 mL, 3.07 mmol) was added. The mixture was stirred at room temperature overnight. 2N HCl was added and the products extracted into EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give the desired product as a white powder. 1H NMR (DMSO-d6, 600 MHz) δ 13.00 (br s, 1H), 8.77 (d, J=7.2 Hz, 1H), 7.92 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 5.45 (d, J=7.2 Hz, 1H), 4.07 (m, 2H), 1.88 (s, 3H), 1.09 (t, J=7.2 Hz, 3H). MS: cal'd 266 (MH+), exp 266 (MH+).

Workup

  1. extractionthe products extracted into EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-0c52c41ced144e0ab7d6d61067365fb7
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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