Lactic Acid → cis-3-t-Butoxycarbonylamino-4-oxo-2-azetidinylmethyl tosylate

HRID 867229Notes

Reaction equation

HRID 867229 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([NH:19][CH:20]1[C:23](=[O:24])[NH:22][CH:21]1[CH2:25][OH:26])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(O)(=O)C(C)O.C(OCC)(=O)C>N1C=CC=CC=1>[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)([O:26][CH2:25][C@H:21]1[C@@H:20]([NH:19][C:17]([O:16][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:18])[C:23](=[O:24])[NH:22]1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 612Lactic AcidHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 14329172tert-Butyl ((2S,3S)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 86735447cis-3-t-Butoxycarbonylamino-4-oxo-2-azetidinylmethyl tosylateYield 71.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.9 g (4.3 mmole) of 98% p-toluenesulfonyl chloride in 10 ml of dry pyridine at 0° is added 0.9 g (4.15 mmole) of 3-t-butoxycarbonylamino-2-hydroxymethyl-4-oxoazetidine. The mixture is stirred for 2 hr at 0° and then stored at 5° overnight. After addition of 0.5 ml of 85% lactic acid, the mixture is stirred for 1 hr, poured into ethyl acetate and washed with dilute HCl, 5% NaHCO3, and brine. The extract is dried over magnesium sulfate and evaporated to dryness to give 1.1 g (70%) of crystalline title product. Recrystallization from hexane-ethyl acetate gives an analytical sample, mp 160°-162° (d).

Workup

  1. waitstored at 5° overnight
  2. stirringthe mixture is stirred for 1 hr
  3. washwashed with dilute HCl, 5% NaHCO3, and brine
  4. dry with materialThe extract is dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9d50103378f840b184a1a11719d9299f
Source dataset
uspto-grants-1978_07
Patent number
US04103086

Reaction notes

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