2-Methyl-2-butene → HCID 178441931, compound

HRID 1656033Notes

Reaction equation

HRID 1656033 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][C:12]3[C:13]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:14][N:15]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:16]=3[CH:17]=[O:18])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[NH:38][N:37]=[N:36][N:35]=1.CC(=CC)C.Cl([O-])=[O:45].[Na+].P([O-])(O)(O)=O.[Na+]>C1COCC1.C(O)(C)(C)C.O>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][C:12]3[C:13]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:14][N:15]([CH2:19][C:20]([F:22])([F:21])[F:23])[C:16]=3[C:17]([OH:45])=[O:18])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[NH:38][N:37]=[N:36][N:35]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 178441928HCID 178441928, compound

Product 1

HCID 178441931HCID 178441931, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 6 (0.3 g) and 2-methyl-but-2-ene (2M in THF; 4 ml) in a mixture of THF (14 ml) and t-butanol (14 ml) was treated with a solution of sodium chlorite (80% tech. 0.55 g), and sodium dihydrogenorthophosphate (0.65 g) in water (10 ml). The mixture was stirred at ambient temperature for 2 h. The solvent was removed in vacuo and the aqueous residue acidified (pH 4.5) with hydrochloric acid (2M). The product was extracted with a mixture of dichloromethane:ethyl acetate (1:1; 25 ml) and the organic extract dried and evaporated in vacuo. The residue was crystallized from methyl acetate/hexane to give the title compound as a white solid (0.2 g), m.p. 216°-220°.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe product was extracted with a mixture of dichloromethane:ethyl acetate (1:1; 25 ml)
  3. extractionthe organic extract
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was crystallized from methyl acetate/hexane

Sources & evidence

ORD record
ord-9abafac79894402cb8970d75941609a5
Source dataset
uspto-grants-1993_10
Patent number
US05252593

Reaction notes

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