HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

TBAF tetrahydrofuran → 1-allyl-3-(S)-hydroxymethyl-4-(R)-phenylsulphonyl-2-azetidinone

HRID 65436
Notes
Print preview

Reaction equation

HRID 65436 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:45]([N:48]([CH2:54][S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56])[C:49](=[O:53])[C@@H:50]1[O:52][CH2:51]1)[CH:46]=[CH2:47]>O1CCCC1>[CH2:45]([N:48]1[C@H:54]([S:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)(=[O:57])=[O:56])[C@@H:50]([CH2:51][OH:52])[C:49]1=[O:53])[CH:46]=[CH2:47]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11078149TBAF tetrahydrofuranHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 53927716N-allyl-N-phenylsulphonylmethyl-(R)-glycidic acid amide

Product 1

HCID 186047761-allyl-3-(S)-hydroxymethyl-4-(R)-phenylsulphonyl-2-azetidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 ml of a tetra-n-butylammonium fluoride/THF solution which has been prepared from 5 g of tetra-n-butylammonium fluoride trihydrate by drying at 60°/0.1 torr and making up to 20.0 ml with tetrahydrofuran is added to a solution of 201 mg (0.757 mmol) of N-allyl-N-phenylsulphonylmethyl-(R)-glycidic acid amide in 1 ml of tetrahydrofuran. The resulting reaction mixture is stirred for 2 hours at 0° and then partitioned between methylene chloride and phosphate buffer solution having a pH of 8.0. The crude product isolated from the organic layer by means of concentration by evaporation is chromatographed over preparative silica gel plates in ethyl acetate/hexane (2:1) and the title compound is obtained in the form of a colourless oil.

Workup

  1. customby drying at 60°/0.1 torr
  2. customThe resulting reaction mixture
  3. custompartitioned between methylene chloride and phosphate buffer solution
  4. customThe crude product isolated from the organic layer by means of concentration by evaporation
  5. customis chromatographed over preparative silica gel plates in ethyl acetate/hexane (2:1)

Sources & evidence

ORD record
ord-ca824bbc1c4944458d3aa5974f6984c1
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04614614

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes