N-Carbethoxyphthalimide → HCID 70530811, compound

HRID 355259Notes

Reaction equation

HRID 355259 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-91b587756cc245619d558b2ee1aa2ad8
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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