Hydrochloric Acid → HCID 86762372, compound

HRID 2369435Notes

Reaction equation

HRID 2369435 reaction equation
[C:1]12[C:12]([O:13][CH:14]3[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OCCCC)[CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][C:8]=1[S:7][C:6]1[CH2:5][CH2:4][CH2:3][C:2]2=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:1]12[C:12]([O:13][CH:14]3[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][C:8]=1[S:7][C:6]1[CH2:5][CH2:4][CH2:3][C:2]2=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86762373HCID 86762373, compound

Product 1

HCID 86762372HCID 86762372, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask placed ten-butyl N-(4-[7-thiatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yloxy]cyclohexyl)carbamate (200 mg, 0.52 mmol, 1.00 equiv) in 16 mL of dichloromethane was added hydrochloric acid (0.5 mL) at 0° C. The resulting solution was stirred for 2 h at room temperature. Then the pH value was adjusted to 8-9 with saturated aqueous sodium carbonate and extracted with 3×50 mL of ethyl acetate and the organic layers combined. The organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give the resulted 4-[7-thiatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yloxy]cyclohexan-1-amine (140 mg, 90% purity) as a white solid which was used for next step without further purification. MS (ES, m/z): 290 (M+H+).

Workup

  1. customInto a 50-mL round-bottom flask placed
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3545fa63a0c2479db14dd40b090f73bb
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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