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

HRID 2259842Notes

Reaction equation

HRID 2259842 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 165 mL of isoamylamine in 150 mL of isopropyl alcohol was heated to reflux for 2.5 hours. The solution was cooled to room temperature, concentrated in vacuo and then recrystallized. The product was isolated by filtration and from ethylacetate/hexane to afford 31.7 g (81%) of N[3(S)-benzyloxycarbonylamino-2(R)-hydroxy-4-phenylbutyl]N-isoamylamine.

Workup

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

Sources & evidence

ORD record
ord-5671e58418104c5087660fc5c7ce5d64
Source dataset
uspto-grants-1995_12
Patent number
US05475027

Reaction notes

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