2-Naphthol → Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl Ether

HRID 1067101Notes

Reaction equation

HRID 1067101 reaction equation
[CH2:1]([N:8]([CH3:23])[C@H:9]([CH2:21][OH:22])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[OH:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NC(N=NC(NC(C)C)=O)=O)(C)C>ClCCl>[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[O:34][C:21](=[O:22])[C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:23]

Participants

6

Reactant 4

HCID 86632-NaphtholHCID 11776TriphenylphosphineHCID 53765619HCID 53765619, compoundHCID 131722659Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithinol

Product 1

HCID 131722658Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl EtherYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A μιξτυρε Oφ Nα-benzyl-Nδ-Boc-Nα-methylornithinol (168 mg), dichloromethane (10 ml), 2-naphthol (91 mg), triphenylphosphine (165 mg), and N,N′-diisopropylazodicarboxamide (124 μl) was stirred for 12 hrs at 25° C., under nitrogen. The reaction mixture was poured into dichloromethane and washed successively with saturated sodium bicarbonate and brine. The organic phase was then dried over anhydrous sodium sulfate and concentrated in vacuo. Further purification by flash chromatography gave the titled product (90 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ1.51 (s, 9H), 1.68 (m, 2H), 1.75 (m, 2H), 2.39 (s, 3H), 3.20 (m, 2H), 3.82 (d, J=13.3, 1H), 3.93 (d, J=13.2, 1H), 4.11 (dd, J=9.6; 3.6, 1H), 4.29 (dd, J=10.2; 8.4, 1H), 7.22 (m, 2H), 7.29 (t, J=7.8, 1H), 7.39 (m, 5H), 7.50 (t, J=8.0, 1H), 7.79 (m, 3H).

Workup

  1. washwashed successively with saturated sodium bicarbonate and brine
  2. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customFurther purification by flash chromatography

Sources & evidence

ORD record
ord-6242f2a9d4464fb68542f2ac1c771d89
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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