Hydrochloric Acid → HCID 131737047, compound

HRID 58985Notes

Reaction equation

HRID 58985 reaction equation
[C:1]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:4]=[C:3]([CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][CH2:32][NH:33]C(=O)OC(C)(C)C)[CH:2]=1.[ClH:47]>>[ClH:47].[C:1]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH:4]=[C:3]([CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH:2]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131737041Di-tert-butyl ((((([1,1'-biphenyl]-3,5-diylbis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

Product 1

HCID 131737047HCID 131737047, compoundYield 60%

Procedure

To the crude di-tert-butyl ((((([1,1′-biphenyl]-3,5-diylbis(methylene))bis(azanediyl))bis(propane-3,1-diyl))bis(azanediyl))-bis(propane-3,1-diyl))dicarbamate from Step 2 was subjected to acidification with methanolic HCl (200 mL, 1.0M). The reaction mixture stirred at rt for 2 h. The reaction mixture was concentrated under reduced pressure, and the solid was collected by vacuum filtration and washed with Et2O (50 mL) and hot MeOH (50 mL) to afford the desired product (6.8 g, 60%) as a white solid. 1H NMR (500 MHz, D2O) δ 7.85 (s, 2H), 7.74 (d, J=7.5 Hz, 2H), 7.59-7.56 (m, 3H), 7.50-7.49 (m, 1H), 4.38 (s, 4H), 3.29 (t, J=8.0 Hz, 4H), 3.23 (q, J=5.0 Hz, 8H), 3.14 (t, J=8.0 Hz, 4H), 2.25-2.19 (m, 4H), 2.17-2.11 (m, 4H). LRMS [M+H]+441.4.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationthe solid was collected by vacuum filtration
  3. washwashed with Et2O (50 mL) and hot MeOH (50 mL)

Sources & evidence

ORD record
ord-46e5a09a93a7485dae7453407f5fb2da
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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