1,4-Dioxane hydrochloride → HCID 59622872, compound

HRID 517664Notes

Reaction equation

HRID 517664 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:18][CH2:19][N:20]2[CH2:28][CH2:27][N:26]([CH2:29][C:30](=[O:36])[O:31]C(C)(C)C)[CH2:25][CH2:24][N:23]([CH2:37][C:38]([O:40]C(C)(C)C)=[O:39])[CH2:22][CH2:21]2)[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])=[CH:4][CH:3]=1.Cl.O1CCOCC1>C(OCC)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]([CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][N:23]([CH2:37][C:38]([OH:40])=[O:39])[CH2:24][CH2:25][N:26]([CH2:29][C:30]([OH:36])=[O:31])[CH2:27][CH2:28]2)[CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59622792HCID 59622792, compound

Product 1

HCID 59622872HCID 59622872, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To Compound 9 (39 mg, 62.9 μmol) with an ice cooling bath around was added 6 mL of 4 M HCl/dioxane dropwise. After the addition was complete, the reaction mixture was gradually warmed to room temperature and allowed to stir overnight at room temperature. After completion 50 mL of ethyl ether was added to the reaction mixture with vigorous stirring and the resulting slurry was kept in the freezer for 2 h. The precipitate was collected and washed with ethyl ether, then immediately lyophilized with water and evaporated to provide pure salt as light yellow solid Compound 10 (34 mg, 85%). NMR (D2O, 300 MHz) δ 2.97 (m, 4H), 3.21 (m, 6H), 3.33 (s, 4H), 3.48 (t, J=5.4 Hz, 2H), 3.93 (s, 4H), 3.99 (s, 2H), 4.46 (s, 2H), 7.40 (d, J=6.4 Hz, 2H), 7.59 (d, J=6.4 Hz, 2H).

Workup

  1. additionAfter the addition
  2. stirringwith vigorous stirring
  3. waitthe resulting slurry was kept in the freezer for 2 h
  4. customThe precipitate was collected
  5. washwashed with ethyl ether
  6. customevaporated

Sources & evidence

ORD record
ord-757c13486a524676832e5bbd7a82d48c
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

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