Citric Acid → HCID 59127832, compound

HRID 654316Notes

Reaction equation

HRID 654316 reaction equation
CON(C)[C:4](=[O:18])[C@H:5]([CH2:14][CH:15]([CH3:17])[CH3:16])[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH:20]([Mg]Br)=[CH2:21].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:10]([O:9][C:7]([NH:6][C@@H:5]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:4](=[O:18])[CH:20]=[CH2:21])=[O:8])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 11119284(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideHCID 178418507HCID 178418507, compound

Product 1

HCID 59127832HCID 59127832, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.01 g (3.69 mmol) of the resultant compound of Example 29 in 50 ml of anhydrous tetrahydrofuran was cooled under N2 atmosphere to -78° C. and treated with 16 ml (9.6 mmol) of vinylmagnesium bromide (0.6M in tetrahydrofuran). The resulting solution was allowed to warm to ambient temperature, stirred for 1.5 h, and poured over a mixture of ice and 10% aqueous citric acid. The mixture was extracted with ether, washed with saturated brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography of the residue using 12% ethyl acetate in hexane provided 0.48 g (58%) of the desired compound (Rf 0.48, 7:3 hexane:ethyl acetate). 1H NMR (CDCl3) δ 0.93 (d, J=7 Hz, 3 H), 1.00 (d, J=7 Hz, 1 H), 1.3-1.45 (m, 2 H), 1.43 (s, 9 H), 1.74 (m, 1 H), 4.65 (td, J=9, 4 H, 1 H), 5.09 (br d, 1 H), 5.88 (dd, J=10, 2 Hz, 1 H), 6.38 (dd, J=18, 2 Hz, 1 H), 6.48 (dd, J=18, 10 Hz, 1 H). Mass spectrum: (M+H)+ =242.

Workup

  1. extractionThe mixture was extracted with ether
  2. washwashed with saturated brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfa2ad88e56040d6b75616a5b8a9b6f7
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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