Hydrochloric Acid → HCID 12653778, compound

HRID 751606Notes

Reaction equation

HRID 751606 reaction equation
[CH3:1][N:2]([CH3:21])[C:3](=[O:20])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[ClH:22]>CO>[ClH:22].[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([N:2]([CH3:21])[CH3:1])=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14541824tert-Butyl (S)-(1-(dimethylamino)-1-oxo-3-phenylpropan-2-yl)carbamate

Product 1

HCID 12653778HCID 12653778, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-tert-butyloxycarbonyl-(S)-phenylalanine dimethylamide (Preparation 7, 24.8 g, 84 mmol) in methanol (50 mL) was added a solution of hydrochloric acid (4N, in dioxane, 40 mL) and the mixture stirred at rt for 3 h. The resulting solution was concentrated in vacuo then dissolved in water (300 mL). The aqueous solution was washed with ethyl acetate (3×100 mL) and concentrated again. Successive recrystallisations with methanol (200 mL) and a mixture of methanol and toluene (1:1, 200 mL) gave the title compound as colourless crystals. δH (D2O) 2.75, 2.90 (6H, 2×s), 3.18 (2H, m), 4.72 (1H, t), 7.28–7.45 (5H, m).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. dissolutionthen dissolved in water (300 mL)
  3. washThe aqueous solution was washed with ethyl acetate (3×100 mL)
  4. concentrationconcentrated again
  5. customSuccessive recrystallisations with methanol (200 mL)
  6. additiona mixture of methanol and toluene (1:1, 200 mL)

Sources & evidence

ORD record
ord-800ae608e887474994ecf23d3566a9fd
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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