Methanol → HCID 131723648, compound

HRID 1018757Notes

Reaction equation

HRID 1018757 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:17][C:18]1([CH3:35])[O:23][C:22]2[C:24]3[C:29]([C:30]([C:32](=[O:33])[C:21]=2[CH2:20][CH:19]1O)=[O:31])=[CH:28][CH:27]=[CH:26][CH:25]=3.C1CCN2C(=NCCC2)CC1.CO>CN(C=O)C.C(Cl)Cl>[NH:1]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:17][C:18]1([CH3:35])[O:23][C:22]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]([C:32](=[O:33])[C:21]=2[CH2:20][CH2:19]1)=[O:31]

Participants

7

Reactant 4

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 1462523-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione

Product 1

HCID 131723648HCID 131723648, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.820 g (12.20 mmol) of Boc-Leu and 1.976 g (12.19 nmmol) of 1,1-carbonyldiimidazole in 33 mL of DMF was stirred at room temperature for 20 min. To the solution was added 2.100 g (8.130 nmol) of 3-hydroxy-β-lapachone followed by 1.6 mL (10.70 mmol) of DBU. After stirring at room temperature for 5 hr, the reaction mixture was partitioned between 200 mL of water and 200 mL of CHCl3. The aqueous phase was washed with CHCl3 (4×50 mL). The CHCl3 extracts were combined, dried with MgSO4, and evaporated to dryness. Column chromatography on silica gel with 2% MeOH in CH2Cl2 afforded 2.038 g (53%) of quinone as an orange glassy solid (and mixture of two diastereomers): Rf=0.45 (5% MeOH in CH2Cl2); 1H NMR (250 MHz, acetone-d6, TMS) δ8.1-8.0 (m, 1H), 8.0-7.9 (m, 1H), 7.9-7.8 (m, 1H), 7.7-7.6 (m, 1H), 6.34 (br d, NH), 5.2-5.1 (m, 1H), 4.2-4.1 (m, 1H), 2.9-2.8 (m, 1H), 2.7-2.5 (m, 1H), 1.8-1.6 (m, 3H), 1.56 (s, 1.5H), 1.53 (s, 3H), 1.52 (s, 1.5H), 1.34 (s, 4.5H), 1.33 (s, 4.5Hd), 0.91 (d, J=7.0Hz, 1.5H), 0.88 (d, J=6.7 Hz, 1.5H), 0.84 (d, J=6.3 Hz, 1.5H), 0.82 (d, J=6.1 Hz, 1.5H).

Workup

  1. customthe reaction mixture was partitioned between 200 mL of water and 200 mL of CHCl3
  2. washThe aqueous phase was washed with CHCl3 (4×50 mL)
  3. dry with materialdried with MgSO4
  4. customevaporated to dryness
  5. customColumn chromatography on silica gel with 2% MeOH in CH2Cl2 afforded

Sources & evidence

ORD record
ord-7e5b045121374483875068012e15dce2
Source dataset
uspto-grants-2002_11
Patent number
US06482943B1

Reaction notes

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