Water → 4-Chloromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetamido]-2-oxo-azetidine

HRID 345646Notes

Reaction equation

HRID 345646 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][C:32]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].S(Cl)(C1C=CC(C)=CC=1)(=O)=O.Cl.[Cl:64][CH2:65][CH:66]1[NH:69][C:68](=[O:70])[CH:67]1[NH2:71].O>C(Cl)Cl.C(N(CC)CC)C>[Cl:64][CH2:65][CH:66]1[NH:69][C:68](=[O:70])[CH:67]1[NH:71][C:27](=[O:28])[C:26]([C:24]1[N:25]=[C:21]([NH:20][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[S:22][CH:23]=1)=[N:30][O:31][C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 199921134-Chloromethyl-3-amino-2-oxo-azetidine hydrochlorideHCID 86743756Sodium 2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetic acid

Product 1

HCID 536478054-Chloromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetamido]-2-oxo-azetidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.527 g of the syn isomer of sodium 2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetic acid, 419 mg of tosyl chloride and 15 ml of methylene chloride was stirred for 40 minutes and then a solution of 342 mg of 4-chloromethyl-3-amino-2-oxo-azetidine hydrochloride in 15 ml of methylene chloride and 0.6 ml of triethylamine was added thereto. The mixture was stirred for 2 hours and water was added thereto with stirring. The decanted aqueous phase was extracted with methylene chloride and the combined organic phases were dried, filtered and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with ether to obtain 736 mg of syn isomer of 4-chloromethyl-3-[2-(2-tritylamino-4-thiazolyl)-2-trityloxyimino-acetamido]-2-oxo-azetidine.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. stirringwith stirring
  3. extractionThe decanted aqueous phase was extracted with methylene chloride
  4. customthe combined organic phases were dried
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was chromatographed over silica gel
  8. washwas eluted with ether

Sources & evidence

ORD record
ord-8bc9b9e7bcff4201a5d63c1aea5eff1e
Source dataset
uspto-grants-1991_10
Patent number
US05057512

Reaction notes

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