Hydrochloric Acid → HCID 178511555, compound

HRID 1984893Notes

Reaction equation

HRID 1984893 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][NH:15]C2N=C(N(C)C)C3C(=CC=CC=3)N=2)[CH2:10][CH2:9]1)(C)(C)C.Cl.[CH3:31][CH2:32][O:33][C:34](C)=[O:35]>>[CH2:32]([O:33][C:34](=[O:35])[NH:15][CH2:14][C@H:11]1[CH2:12][CH2:13][C@@H:8]([NH2:7])[CH2:9][CH2:10]1)[C:31]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 178483073HCID 178483073, compound

Product 1

HCID 178511555HCID 178511555, compoundYield 95%

Procedure

To a solution of cis-[4-(benzyloxycarbonylamino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester obtained in step C of example 23 (12.9 g, 35.6 mmol) in EtOAc (129 mL) was added 4 M hydrogen chloride in EtOAc (129 mL). The reaction mixture was stirred at ambient temperature for 3 hr, filtered, washed with EtOAc, and dried under reduced pressure. The solid was dissolved in saturated aqueous NaHCO3. The aqueous layer was extracted with CHCl3 (five times), dried over MgSO4, filtered and concentrated, and dried under reduced pressure to give cis-(4-amino-cyclohexylmethyl)-carbamic acid benzyl ester (8.88 g, 95%) as a colorless oil.

Workup

  1. filtrationfiltered
  2. washwashed with EtOAc
  3. customdried under reduced pressure
  4. dissolutionThe solid was dissolved in saturated aqueous NaHCO3
  5. extractionThe aqueous layer was extracted with CHCl3 (five times)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-0c4d65c399aa495fb13f60439cf45f0b
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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