Diisopropylethylamine → HCID 57127861, compound

HRID 325005Notes

Reaction equation

HRID 325005 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]1[C@@H:16]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[NH:15][C:14]1=[O:22].C(N(C(C)C)CC)(C)C.[I:32][C:33]1[CH:38]=[CH:37][C:36]([C:39](Cl)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:35][CH:34]=1>CC(C)=O>[I:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]([NH:12][C@H:13]2[C@@H:16]([O:17][CH2:18][CH:19]([CH3:20])[CH3:21])[NH:15][C:14]2=[O:22])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18425159HCID 18425159, compoundHCID 86585377HCID 86585377, compound

Product 1

HCID 57127861HCID 57127861, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of (3S,4R)-3-amino-4-(isobutoxy)azetidin-2-one para-toluenesulfonate (180 mg, 0.54 mmol) in acetone (8 mL) containing diisopropylethylamine ( 1.1 mmol) was treated with a solution of (4-iodophenyl)diphenylmethyl chloride (218 mg, 0.54 mmol), prepared as described by Tschitschibabin, Chem. Ber. 44, 450 (191 1), in acetone (98 mL). The solution was stirred for 6 h and partitioned between water and dichloromethane. The combined organic phases were dried (magnesium sulfate), concentrated, and the residue was chromatographed on silica gel eluted with 15% ethyl acetate:hexane to give the title compound (190 mg, 67%). MS(ES) m/e 527 [M+H]+.

Workup

  1. customprepared
  2. custompartitioned between water and dichloromethane
  3. dry with materialThe combined organic phases were dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel
  6. washeluted with 15% ethyl acetate

Sources & evidence

ORD record
ord-e725df9f3d14445bb2ee4668d4890223
Source dataset
uspto-grants-2001_04
Patent number
US06221860B1

Reaction notes

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