N-Carbethoxyphthalimide → HCID 70530811, compound

HRID 1680356Notes

Reaction equation

HRID 1680356 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:6]([S:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4]1=[O:27].C(N1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43])(OCC)=O>C1C=CC=CC=1>[C:34]1(=[O:43])[N:1]([CH2:2][C@H:3]2[C@H:6]([S:7][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:5][C:4]2=[O:27])[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]12

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 12822421HCID 12822421, compound

Product 1

HCID 70530811HCID 70530811, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of trans 3-aminomethyl-4-tritylthio-2-azetidinone (13.9 g, 37.2 mmol) and N-carbethoxyphthalimide (8.3 g, 37.9 mmol) in benzene (200 ml) was heated under reflux for 15 h. The solvent was evaporated in vacuo and the residue crystallized from ether to give 17.4 g (93%) of the title compound; mp 172°-3° C.; Anal. calcd for C31H24N2O3S: C 73.78, H 4.79, N 5.55, found: C 73.92, H 4.87, N 5.49; ir (CHCl3) νmax : 1770 and 1715 cm-1 ; 1Hmr (CDCl3) δ: 7.8 (4H, m), 7.3 (15H, m), 4.45 (1H, d, J=2 Hz), 3.3-4.1 (3H, m) and 3.3-4.6 ppm (1H, m).

Workup

  1. temperatureunder reflux for 15 h
  2. customThe solvent was evaporated in vacuo
  3. customthe residue crystallized from ether

Sources & evidence

ORD record
ord-3fcd5d5f64ed4c698ae5c1fdaa0ed82c
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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