Triethylamine → HCID 3729695, compound

HRID 617899Notes

Reaction equation

HRID 617899 reaction equation
C([O:3][P:4]([CH2:9][C:10]1([C:15]([NH:17][C@H:18]2[CH2:24][CH2:23][C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[N:20]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:19]2=[O:35])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)([O:6]CC)=[O:5])C.Br[Si](C)(C)C.C([N:43](CC)CC)C>ClCCl.CC(C)=O>[P:4]([CH2:9][C:10]1([C:15]([NH:17][C@H:18]2[CH2:24][CH2:23][C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[N:20]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:19]2=[O:35])=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14]1)([OH:5])([OH:6])=[O:3].[CH3:24][CH:23]([NH3+:43])[C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:21]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 76113BromotrimethylsilaneHCID 15859185HCID 15859185, compound

Product 2

HCID 3729695HCID 3729695, compoundHCID 15859183HCID 15859183, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

1.3 g of ethyl (3S)-3-(1-diethylphosphono-methylcyclopentane-1-carbonylamino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (preparation see Example 12) were dissolved in 13 ml of dry dichloromethane under a nitrogen atmosphere. 0.5 ml of bromotrimethylsilane and 0.4 ml of triethylamine were added with ice-cooling and the mixture was stirred over night. Excess solvent was stripped off in vacuo, and the residue was stirred in aqueous acetone for 15 minutes. The residue which remained after evaporation of the solvent was taken up in MTBE to which a little dichloromethane had been added and treated with 0.53 g of S-(-)-α-methylbenzylamine. The precipitated solid was recryatallized once from ethanol, the title compound being obtained as the α-methylbenzylammonium salt of m.p.=210-213° C. IR=2940, 1750, 1650, 1200, 1045 cm-1 (KBr); [α]D20 32 -141.0° (c=0.2 in methanol).

Workup

  1. temperaturecooling
  2. customafter evaporation of the solvent
  3. additionhad been added
  4. additiontreated with 0.53 g of S-(-)-α-methylbenzylamine

Sources & evidence

ORD record
ord-44d63289fdcc420f9d812c0e360393ff
Source dataset
uspto-grants-1999_09
Patent number
US05952327

Reaction notes

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