Phenylacetyl chloride → HCID 70575130, compound

HRID 1680004Notes

Reaction equation

HRID 1680004 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:23][CH:24]1[C:51](=[O:52])[N:26]2[CH:27]([C:41]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[O:42])[C:28]3([S:40][C@H:25]12)[CH2:33][CH2:32][N:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:30][CH2:29]3.C(N(CC)CC)C.[C:60]1([CH2:66][C:67](Cl)=[O:68])[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>ClCCl>[C:34]1([N:31]2[CH2:32][CH2:33][C:28]3([CH:27]([C:41]([O:43][CH2:44][C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)=[O:42])[N:26]4[C:51](=[O:52])[CH:24]([NH:23][C:67](=[O:68])[CH2:66][C:60]5[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=5)[C@H:25]4[S:40]3)[CH2:29][CH2:30]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471Triethylamine2×HCID 86737760HCID 86737760, compound

Product 1

HCID 70575130HCID 70575130, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
15 °C

Procedure

To a suspension of 1.53 g (0.002 mole) of benzyl 6-amino-1'-phenyl-spiro[penam-2,4'-piperidine]-3-carboxylate di-p-toluenesulfonate (prepared according to the method described in Example 1.8.3. of our Application Ser. No. 06/162,616, filed June 24, 1980) in 100 ml of anhydrous dichloromethane is added all at once 404 mg (0.004 mole) of triethylamine in 10 ml of dichloromethane. The solution is cooled to a temperature of from 0° to -5° C. and then there are simultaneously added dropwise a solution of 340 mg (0.022 mole) of phenylacetyl chloride in 30 ml of dichloroemethane and a solution of 220 mg (0.022 mole) of triethylamine in 30 ml of dichloromethane, the addition taking place over the course of about 1 hour. Thereafter, the reaction mixture is stirred for 3 hours at 15° C., then successively washed with water, with a saturated aqueous solution of sodium hydrogen carbonate and again with water. After evaporating the solution to dryness and recrystallizing the residue from ethyl acetate/hexane (1:3 v/v), there are obtained 950 mg of benzyl 1'-phenyl-6-(2-phenylacetamido)-spiro[penam-2,4'-piperidine]-3-carboxylate. Yield: 88%; M.P. 120°-121° C.

Workup

  1. customprepared
  2. temperatureThe solution is cooled to a temperature of from 0° to -5° C.
  3. customover the course of about 1 hour
  4. washsuccessively washed with water, with a saturated aqueous solution of sodium hydrogen carbonate and again with water
  5. customAfter evaporating the solution to dryness
  6. customrecrystallizing the residue from ethyl acetate/hexane (1:3 v/v), there

Sources & evidence

ORD record
ord-85b8223a4089497ebf5ca576f89f2c1d
Source dataset
uspto-grants-1981_06
Patent number
US04271173

Reaction notes

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