Hydrochloric Acid → HCID 86676469, compound

HRID 532133Notes

Reaction equation

HRID 532133 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[NH:5][CH:6]1[CH:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)[CH:13]=2)[O:8][CH2:7]1)[CH3:2].[ClH:35]>C(Cl)Cl.C(O)(C)C>[ClH:35].[NH2:26][CH2:25][CH2:24][O:23][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH:6]([NH:5][C:4](=[O:34])[O:3][CH2:1][CH3:2])[CH:15]2[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71245505HCID 71245505, compound

Product 1

HCID 86676469HCID 86676469, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

487 mg (1.04 mmol) of [4-benzyl-6-(2-tert-butoxycarbonylamino-ethoxy)-chroman-3-yl]-carbamic acid ethyl ester were dissolved in 10 ml methylene dichloride and 2 ml of a solution of hydrogen chloride in isopropanol (5-6 N) were added and the mixture was stirred over night at room temperature. The reaction mixture was warmed to 40° C., stirred for additional 45 min, and concentrated. The residue was dissolved in water and washed with ether. The aqueous phase was concentrated and the residue co-distilled with toluene to give 463 mg (1.14 mmol, quant.) of the desired product.

Workup

  1. temperatureThe reaction mixture was warmed to 40° C.
  2. stirringstirred for additional 45 min
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in water
  5. washwashed with ether
  6. concentrationThe aqueous phase was concentrated

Sources & evidence

ORD record
ord-5bae5e36b5584382b629093c03f7d9ac
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

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