Diisopropylethylamine → HCID 57611928, compound

HRID 1919880Notes

Reaction equation

HRID 1919880 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.[O:26](C(OC(C)(C)C)=O)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=O>C1COCC1.CCOC(C)=O>[C:30]([O:29][C:27]([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:26])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 57611946HCID 57611946, compound

Product 1

HCID 57611928HCID 57611928, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(1-amino-2-ethoxy-2-oxoethyl)benzoic acid, as described in Example 1, Step B, (0.8 g, 3.58 mmol) and DIPEA (1.377 mL, 7.88 mmol) were suspended in THF (8 mL) and BOC2O (0.915 mL, 3.94 mmol) was added. The solution was stirred at room temperature for 2 days. The reaction mixture was diluted with EtOAc, washed with 2N HCl and brine, dried over MgSO4 and concentrated in vacuo to give the desired product as a colorless gum. 1H NMR (DMSO-d6, 600 MHz) δ 12.95 (br s, 1H), 7.88 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.4 Hz, 1H), 7.48 (d, J=8.4 Hz, 2H), 5.25 (d, J=8.4 Hz, 1H), 4.06 (m, 2H), 1.36 (s, 9H), 1.09 (t, J=7.2 Hz, 3H). MS: cal'd 324 (MH+), exp 224 (MH+).

Workup

  1. washwashed with 2N HCl and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e922171ea9ed408f8f547fcb83e8f3ad
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

Loading…