Hydrochloric Acid → Ammonia

HRID 2206948Notes

Reaction equation

HRID 2206948 reaction equation
C(OC([NH:8][CH:9]([CH2:19][CH:20]([O:22][CH2:23][CH2:24][F:25])[CH3:21])[CH:10]([C:15]([O:17]C)=[O:16])[C:11]([O:13]C)=[O:12])=O)(C)(C)C.Cl>CO>[NH2:8][CH:9]([CH2:19][CH:20]([O:22][CH2:23][CH2:24][F:25])[CH3:21])[CH:10]([C:15]([OH:17])=[O:16])[C:11]([OH:13])=[O:12].[NH3:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86644800HCID 86644800, compound

Product 2

HCID 222AmmoniaYield 5%HCID 86644799HCID 86644799, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg of dimethyl 3-tert-butoxycarbonylamino-4-(2-fluoroethoxy)pentanedicarboxylate (27) were dissolved in 50 ml of MeOH and treated with stirring with 1 ml of HCl (6N). The reaction mixture was heated to reflux for 15-20 min, concentrated to dryness, diluted with 50 ml of water, and the hydrochloride was filtered off and carefully washed with 3×5 ml of water. The amino acid 28 was isolated by means of ion exchange chromatography on a 50 w×8 Dowex column in H+ form (eluent: 5% NH3 aq).

Workup

  1. additiontreated
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 15-20 min
  4. concentrationconcentrated to dryness
  5. additiondiluted with 50 ml of water
  6. filtrationthe hydrochloride was filtered off
  7. washcarefully washed with 3×5 ml of water

Sources & evidence

ORD record
ord-d8809fe5d4804e4f8e6beaca6aac813b
Source dataset
uspto-grants-2016_06
Patent number
US09375497B2

Reaction notes

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