Triethylamine → Phthalimide

HRID 2290489Notes

Reaction equation

HRID 2290489 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1OC)[CH2:6][NH2:7].C(=C(O)[C@H](O)[CH:18]=[O:19])(C)C.S([O-])([O-])(=O)=[O:23].[Mg+2].COC1C=C(C=CC=1OC)CN=C[C@H](C(=C(C)C)O)O.C(N(CC)CC)C>C(Cl)Cl>[C:18]1(=[O:19])[NH:7][C:6](=[O:23])[C:5]2=[CH:8][CH:9]=[CH:10][CH:3]=[C:4]12

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 79832VeratrylamineHCID 86741373HCID 86741373, compoundHCID 131714936HCID 131714936, compound

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution, stirred at room temperature, of 0.9 g (5.4 mmol) of 3,4-dimethoxybenzylamine in 100 ml of methylene chloride are added 3 g of molecular sieve 4 Å and after 20 minutes 0.7 g (5.4 mmol) of isopropylidene-L-glyceraldehyde and 5 g of anhydrous magnesium sulphate. The mixture is subsequently stirred at room temperature for 1 hour. The resulting organic solution of isopropylidene-L-glyceraldehyde (3,4-dimethoxybenzyl)imine is cooled to -20° under argon and treated while stirring with 0.88 ml (5.4 mmol) of triethylamine. Then, a solution of 1.25 g (5.6 mmol) of phthaloylglycyl chloride in 20 ml of dry methylene chloride is added dropwise thereto within 1 hour and the mixture is subsequently stirred overnight at room temperature. The mixture is worked-up as described in Example 1 and there are obtained after chromatography 1.56 g (62%) of N-(3S,4S)-cis-1-(3,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinyl]phthalimide as a foam; [α ]D =+16.2° (c=1.0 in methanol); MS: 466 (M+).

Workup

  1. additionare added 3 g of molecular sieve 4 Å
  2. additiontreated
  3. waitwithin 1 hour
  4. waitthe mixture is subsequently stirred overnight at room temperature

Sources & evidence

ORD record
ord-ca4011c7bc2a4194b7f46be77298350a
Source dataset
uspto-grants-1986_10
Patent number
US04617150

Reaction notes

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