2-Naphthol → HCID 131722657, compound

HRID 1067099Notes

Reaction equation

HRID 1067099 reaction equation
[C:1]([NH:8][C@H:9]([CH2:24][OH:25])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[OH:36].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:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[O:36][C:24](=[O:25])[C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 86632-NaphtholHCID 11776TriphenylphosphineHCID 11772551Nalpha-Boc-Ndelta-Cbz-ornithinolHCID 53765619HCID 53765619, compound

Product 1

HCID 131722657HCID 131722657, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Solution of Nα-Boc-Nδ-Cbz-ornithinol (587 mg), dichloromethane (17 ml), 2-naphthol (288 mg), triphenylphosphine (524 mg) and N,N′-diisopropylazodicarboxamide (393 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 (534 mg) as a glassy solid: 1H NMR (400 MHz, CDCl3) δ1.41 (s, 9H), 1.60-1.73 (m, 4H), 3.20 (m, 2H), 4.01 (m, 3H), 5.07 (s, 2H), 7.09 (s, 1H), 7.11 (d, J=8.3 Hz, 1H), 7.28 (m, 6H), 7.40 (t, J=8.4 Hz, 1H), and 7.71 (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-c0cb7b59be25427b809c2803788b6050
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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