Acetic Acid → HCID 18425152, compound

HRID 1280546Notes

Reaction equation

HRID 1280546 reaction equation
[Si]([N:8]1[CH:11]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:10]([NH:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:37])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:13]([O:12][CH:11]1[NH:8][C:9](=[O:37])[CH:10]1[NH:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 18425148HCID 18425148, compound

Product 1

HCID 18425152HCID 18425152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3RS,4RS)-1-(tert-butyldimethylsilyl)-4-(isobutoxy)-3-(triphenylmethylamino)azetidin-2-one (160 mg, 0.3 mmol) in tetrahydrofuran (4 mL) was cooled in an ice bath and treated with acetic acid (25 mg, 0.4 mmol) followed by dropwise addition of 1M tetrabutylammonium fluoride (0.6 mL, 0.6 mmol). The mixture was stirred for 20 min and passed through silica gel (10 g) eluted with ethyl acetate. The eluate was concentrated and the residue was chromatographed on silica gel eluted with 20% ethyl acetate:hexane to give the title compound. MS(ES) m/e 423 [M+Na]+.

Workup

  1. washeluted with ethyl acetate
  2. concentrationThe eluate was concentrated
  3. customthe residue was chromatographed on silica gel
  4. washeluted with 20% ethyl acetate

Sources & evidence

ORD record
ord-1372a30ae9ba4098be12a256f7015ede
Source dataset
uspto-grants-2002_09
Patent number
US06451785B1

Reaction notes

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