Isoamylamine → n[3(s)-Benzyloxycarbonylamino-2(r)-hydroxy-4-phenylbutyl]n-isoamylamine

HRID 1941328Notes

Reaction equation

HRID 1941328 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:13]1[O:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:28])[CH2:24][CH:25]([CH3:27])[CH3:26]>C(O)(C)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:13]([OH:15])[CH2:14][NH:28][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Product 1

HCID 10430124n[3(s)-Benzyloxycarbonylamino-2(r)-hydroxy-4-phenylbutyl]n-isoamylamineYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Part C. A solution of N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane (30.1 g, 0.10 mol) and 165mL of isoamylamine in 150 mL of isopropyl alcohol was heated to reflux for 2.5 hours. The solution was cooled to room temperature, concentrated/n vacuo and then recrystallized. The product was isolated by filtration and from ethylacetate/hexane to afford 1.7 g (81%) of N[3(S)-benzyloxycarbonylamino-2(R)-hydroxy-4-phenylbutyl]N-isoamylamine.

Workup

  1. temperatureto reflux for 2.5 hours
  2. concentrationconcentrated/n vacuo
  3. customrecrystallized
  4. customThe product was isolated by filtration and from ethylacetate/hexane

Sources & evidence

ORD record
ord-c56e3f242c8f4f1996d3dd2e4098b7ab
Source dataset
uspto-grants-1997_12
Patent number
US05703076

Reaction notes

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