Hydrochloric Acid → HCID 178424140, compound

HRID 59771Notes

Reaction equation

HRID 59771 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:19][CH2:18]3)[CH2:10][CH2:9]1)(C)(C)C.[ClH:33]>O1CCOCC1.C(OCC)C>[ClH:33].[C:26]1([CH3:31])[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:20]1[CH2:19][CH2:18][C:17]2[C:22](=[CH:23][CH:24]=[C:15]([O:14][C@H:11]3[CH2:10][CH2:9][C@H:8]([NH2:7])[CH2:13][CH2:12]3)[CH:16]=2)[O:21]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178424143HCID 178424143, compound

Product 1

HCID 178424140HCID 178424140, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

6 g (13.7 mmol) of [trans-4-(2-o-tolyl-chroman-6-yloxy)-cyclohexyl]-carbamic acid tert-butyl ester were dissolved in 50 ml of 1,4-dioxane and 25 ml of 2N hydrogen chloride in diethyl ether. The diethyl ether was removed by evaporation and the remaining solution was refluxed until no starting material could be detected by RP-HPLC. The resulting suspension was cooled to 0° C. and the crystals were collected by filtration, washed once with cold methyl tert-butyl ether and dried in vacuum at 25° C. to yield 3.6 g of the title compound.

Workup

  1. customThe diethyl ether was removed by evaporation
  2. temperaturethe remaining solution was refluxed until no starting material
  3. filtrationthe crystals were collected by filtration
  4. washwashed once with cold methyl tert-butyl ether
  5. customdried in vacuum at 25° C.

Sources & evidence

ORD record
ord-6f02b2dd9f294d90a899b81d5c70b93e
Source dataset
uspto-grants-2016_09
Patent number
US09440941B2

Reaction notes

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