Diazomethane → HCID 54335426, compound

HRID 2291963Notes

Reaction equation

HRID 2291963 reaction equation
[Si:1]([N:8]1[CH:11]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][C:9]1=[O:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:33]1[C:37]([C:38]([O:40]CC)=O)=[N:36][N:35]=[N:34]1.[N+](=[CH2:45])=[N-].N1CCC1=O>C(Cl)Cl>[Si:1]([N:8]1[CH:11]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]([C:38]([C:37]2[N:36]([CH3:45])[N:35]=[N:34][N:33]=2)=[O:40])[C:9]1=[O:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 9550DiazomethaneHCID 1367212-AzetidinoneHCID 129287451-t-Butyldimethylsilyl-4-tritylthio-2-azetidinoneHCID 178470518HCID 178470518, compound

Product 1

HCID 54335426HCID 54335426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-t-Butyldimethylsilyl-4-tritylthioazetidin-2-one (1) (9.18 g, 20 mmol) was reacted with an approximately 1:1 mixture of ethyl 1- and 2-methyltetrazole-5-carboxylate (3.94 g, 24.8 mmol) (prepared by treating ethyl tetrazole-5-carboxylate [D. Moderhack, Chem. Ber., 1975, 108, 887]with excess diazomethane [cf 0. Gryszkiewicz-Trochimourski, Compt. Rendu, 1958, 246, 2627]) using the method described in Preparation 4(a). The crude reaction mixture was chromatographed on silica eluting with ethyl acetate/hexane mixtures to give two fractions. The less polar fraction contained a regioisomer of the title azetidinone (123) (3.48 g, 30%) νmax (CH2Cl2) 1750, 1690 cm-1 ; δ(CDCl3) 0.34 (6H, s), 1.00 (9H, s), 4.10 (3H, s), 4.90 (2H, s), 6.77-7.50 (15H, m); The more polar fraction contained the other regioisomer of the title compound ( 124) (3.5g, 30%) (mp. 158°-161°, needles ex ether/hexane) νmax (CH2Cl2) 1750, 1700 cm-1 ; δ(CDCl3) 0.37 (6H, s), 1.00 (9H, s), 4.37 (3H, s), 4.57 (1H, d, J2 Hz), 4.97 (1H, d, J2 Hz), 6.80-7.60 (15H, m). (Found C, 65.3; H; 6.3; N, 12.2; S, 5.6. C31H35N5O2SSi requires C, 65.4; H, 6.2; N, 12.3; S, 5.6%).

Workup

  1. customprepared
  2. customThe crude reaction mixture
  3. customwas chromatographed on silica eluting with ethyl acetate/hexane
  4. customto give two fractions

Sources & evidence

ORD record
ord-eca3b0d0930d4708b706a5e1e09fcd5e
Source dataset
uspto-grants-1989_01
Patent number
US04798828

Reaction notes

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