Dimethylformamide → HCID 70552031, compound

HRID 1156497Notes

Reaction equation

HRID 1156497 reaction equation
[C:1]1(=[O:24])[N:5]([CH:6]2[C:17](=[O:18])[N:8]3[CH:9]([C:14]([OH:16])=[O:15])[C:10]([CH3:13])([CH3:12])[S:11][C@H:7]23)[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12.C(N(CC)CC)C.[N+:32]([C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1)([O-:34])=[O:33].CN(C)C=O>O>[N+:32]([C:35]1[CH:42]=[CH:41][C:38]([CH2:39][O:15][C:14]([CH:9]2[N:8]3[C:17](=[O:18])[CH:6]([N:5]4[C:4](=[O:19])[C:3]5=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]5[C:1]4=[O:24])[C@H:7]3[S:11][C:10]2([CH3:12])[CH3:13])=[O:16])=[CH:37][CH:36]=1)([O-:34])=[O:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 70553421HCID 70553421, compound

Product 1

HCID 70552031HCID 70552031, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Phthalimido-2,2-dimethyl-penam-3-carboxylic acid p-nitrobenzyl ester is prepared by placing a mixture of 1.0 g. of 6-phthalimido-2,2-dimethyl-penam-3-carboxylic acid, 0.4 ml. of triethylamine, 0.75 g. of p-nitrobenzyl bromide and 10 ml. of dimethyl formamide in a refrigerator for 3 hours. Thereafter, 10 ml. of water are added and the resulting precipitate formed is filtered, washed with acetone and recrystallized from methylethyl ketone to yield colorless crystals; mp 233°-34° C.; nmr (CDCl3) 89(S,3H); 111(S,3H); 287(S,1H); 322(S,2); 338.5(d,1H,J=4.5 Hz); 342(d,1H,J=4.5 Hz); 472 cps (m,8 ArH).

Workup

  1. additiona mixture of 1.0 g
  2. customthe resulting precipitate formed
  3. filtrationis filtered
  4. washwashed with acetone
  5. customrecrystallized from methylethyl ketone
  6. customto yield colorless crystals

Sources & evidence

ORD record
ord-579d4a9ebb3d4decbe1d8d683b171535
Source dataset
uspto-grants-1982_06
Patent number
US04336191

Reaction notes

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