Sodium Chloride → HCID 15221753, compound

HRID 2260397Notes

Reaction equation

HRID 2260397 reaction equation
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[N:11]=[CH:12][N:13]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=2)C=CC=CC=1.C([Li])CCC.CCCCCC.O=[CH:58][CH2:59][C@H:60]([NH:68][C:69]([O:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)=[O:70])[C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62].[Cl-].[Na+]>O1CCCC1>[C:73]1([CH2:72][O:71][C:69]([NH:68][C@@H:60]([CH2:59]/[CH:58]=[CH:9]/[C:10]2[N:11]=[CH:12][N:13]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:14]=2)[C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])=[O:70])[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 10590835AG-H-15125HCID 18800269HCID 18800269, compoundHCID 178418339Butyllithium

Product 1

HCID 15221753HCID 15221753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

50.93 g (820 mmol) of triphenyl[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]phosphonium chloride in solution in 333 ml of tetrahydrofuran are introduced, under argon, into a three-necked round-bottomed flask. 51.2 ml of a 1.6M solution of n-butyllithium in hexane (820 mmol) are added dropwise, at -70° C. After stirring for 30 minutes at -70° C., the reaction mixture is quickly poured into 270 ml of a 0.253M solution, cooled to -70° C., of 1,1-dimethylethyl (S)-4-oxo-2-[[(phenylmethoxy)carbonyl]amino]butanoate in tetrahydrofuran (683 mmol). The mixture is allowed to return to room temperature overnight. The mixture is hydrolysed with 280 ml of a saturated aqueous sodium chloride solution. The aqueous phase is separated from the organic phase and extracted with 2 times 140 ml of ethyl acetate. The organic phases are combined, dried over magnesium sulphate and evaporated to dryness. Purification is carried out by chromatography on a column of silica gel, the eluent being a hexane/ethyl acetate gradient.

Workup

  1. waitto return to room temperature overnight
  2. customThe aqueous phase is separated from the organic phase
  3. extractionextracted with 2 times 140 ml of ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness
  6. customPurification

Sources & evidence

ORD record
ord-f2b997695b3048bbb07236f28a4c217a
Source dataset
uspto-grants-1995_12
Patent number
US05476942

Reaction notes

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