Triethylamine → HCID 86754459, compound

HRID 617895Notes

Reaction equation

HRID 617895 reaction equation
C([O:3][P:4]([CH2:7][C:8]1([C:13]([NH:15][C@H:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:18]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]2=[O:33])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)([OH:6])=[O:5])C.C(N([CH2:39][CH3:40])CC)C.[C:41]([O:47][CH2:48]Cl)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43].CN(C1C=CC=CN=1)C>CN(C=O)C>[C:41]([O:47][CH2:48][C:7]([CH2:39][CH3:40])([P:4]([OH:6])([OH:3])=[O:5])[C:8]1([C:13]([NH:15][C@H:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:18]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]2=[O:33])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 87885Chloromethyl pivalateHCID 57095452HCID 57095452, compound

Product 1

HCID 86754459HCID 86754459, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.6 g of ethyl (3S)-3-(1-ethylphosphonomethyl-cyclopentane-1-carbonylamino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (preparation see Example 5) was dissolved in 20 ml of DMF with exclusion of moisture and then treated with 1.86 ml of triethylamine, 0.88 ml of pivaloyloxymethyl chloride and 0.1 g of dimethylaminopyridine. The reaction mixture was stirred overnight, the solvent was evaporated under reduced pressure and the residue was taken up in dichloromethane. The organic phase was washed with water and then dried over sodium sulfate. Concentration in vacuo yielded a crude product which for purification was chromatographed on 50 g of silica gel (eluent: initially n-hexane/ethyl acetate 3:7, the amount of ester gradually being increased to 100%). 188 mg of the title compound were obtained as an oil, IR=1740, 1650 cm-1 (CH2Cl2); [α]D20 =-124.1° (c=0.228 in methanol).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration in vacuo
  5. customyielded a crude product which
  6. customfor purification
  7. customwas chromatographed on 50 g of silica gel (eluent
  8. temperatureinitially n-hexane/ethyl acetate 3:7, the amount of ester gradually being increased to 100%)

Sources & evidence

ORD record
ord-7a7061314ca144728b8f8d31a2c63fa7
Source dataset
uspto-grants-1999_09
Patent number
US05952327

Reaction notes

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