Hydrochloric Acid → HCID 66656059, compound

HRID 1035226Notes

Reaction equation

HRID 1035226 reaction equation
[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH:15]3[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[NH:17]1[CH2:16][CH:15]([S:14][C:11]2[CH:10]=[CH:9][C:8]([C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[O:7])=[CH:13][CH:12]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58043119HCID 58043119, compound

Product 1

HCID 66656059HCID 66656059, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 59C (1.40 g, 3.89 mmol) in dioxane (20 mL) was added a solution of HCl (4M in dioxane, 20 mL). The mixture was stirred at RT over night and then the solvent was removed by evaporation. The residue was partitioned between DCM and water. The Organic solution was extracted with an aqueous solution of HCl (0.1 M). The combined aqueous solutions were pH adjusted to pH>11 by carefully adding a saturated aqueous solution of Na2CO3. The mixture was extracted several times with DCM. The solvent was removed by evaporation. There was obtained 0.56 g (55%) of 59D as an oil. 1H NMR (500 MHz, CDCl3): δ 1.88 (m, 2H), 1.94 (m, 2H), 3.43 (m, 2H), 3.62 (m, 2H), 3.68 (m, 2H), 4.04 (m, 2H), 4.29 (m, 1H), 7.19 (d, 2H), 7.44 (d, 2H), MS (APCI+) m/z 263 [M+H]+.

Workup

  1. customthe solvent was removed by evaporation
  2. customThe residue was partitioned between DCM and water
  3. extractionThe Organic solution was extracted with an aqueous solution of HCl (0.1 M)
  4. additionby carefully adding a saturated aqueous solution of Na2CO3
  5. extractionThe mixture was extracted several times with DCM
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-13280b9f00f44150986544fc270eba7d
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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