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Boron trifluoride etherate → HCID 86755840, compound

HRID 1954030
Notes
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Reaction equation

HRID 1954030 reaction equation
[CH3:1][CH2:2][C@H:3]1[C:33](=[O:34])[CH2:32][C@H:31]([OH:35])[C@@H:30]([CH3:36])[C@@H:29](/[C:37](/[CH3:48])=[CH:38]/[C@H:39]2[CH2:44][C@@H:43]([O:45][CH3:46])[C@H:42]([OH:47])[CH2:41][CH2:40]2)[O:28][C:26](=[O:27])[C@H:25]2[N:20]([CH2:21][CH2:22][CH2:23][CH2:24]2)[C:18](=[O:19])[C:16](=[O:17])[C@:14]2([OH:49])[O:15][C@@H:10]([C@@H:11]([O:51][CH3:52])[CH2:12][C@H:13]2[CH3:50])[C@@H:9]([O:53][CH3:54])[CH2:8][C@@H:7]([CH3:55])[CH2:6][C:5]([CH3:56])=[CH:4]1.B(F)(F)F.CC[O:63][CH2:64]C.F.[F-].C1(C)C=CC([S:74]([O-:77])(=O)=[O:75])=CC=1.[NH+:79]1[CH:84]=CC=CC=1.BrN1C(=[O:91])CCC1=O.C(B(CC)OB(CC)CC)C.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O>CO.C(Cl)(Cl)Cl.O1CCCC1.C(O)C.CS(C)=O.C(O)(=O)C.O>[CH2:2]([C@@H:3]1[CH:4]=[C:5]([CH3:56])[CH2:6][C@H:7]([CH3:55])[CH2:8][C@H:9]([O:53][CH3:54])[C@H:10]2[O:15][C@:14]([OH:49])([C@H:13]([CH3:50])[CH2:12][C@@H:11]2[O:51][CH3:52])[C:16](=[O:17])[C:18](=[O:19])[N:20]2[C@@H:25]([CH2:24][CH2:23][CH2:22][CH2:21]2)[C:26](=[O:27])[O:28][C@H:29](/[C:37](/[CH3:48])=[CH:38]/[C@@H:39]2[CH2:40][CH2:41][C@@H:42]([O:47][S:74]([NH:79][C:84]([O:63][CH3:64])=[O:91])(=[O:77])=[O:75])[C@H:43]([O:45][CH3:46])[CH2:44]2)[C@H:30]([CH3:36])[C@@H:31]([OH:35])[CH2:32][C:33]1=[O:34])[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

15

Reactant 8

HCID 8000Boron trifluoride etherateHCID 14917Hydrofluoric AcidHCID 28179Fluoride IonHCID 65367Trimethylsilyl triflateHCID 67184N-bromobutanimideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 580351
Borane, oxybis[diethyl-
HCID 5282071Ascomycin

Product 1

HCID 86755840HCID 86755840, compound

Reagents, catalysts & solvents 6

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of chlorosulfonylisocyanate (4.36 ml, 0.05 mol) in benzene (15 mL) was placed into a three necked flask, equipped with a thermometer, a droping funnel and a reflux condenser under a nitrogen atmosphere. The flask was immersed in a water bath. A solution of methanol (2.02 mL, 0.05 mmol) in 3 ml of benzene was added dropwise such that the temperature was maintained in a range of 25-30° C. After complete addition, the mixture was stirred for an additional 30 minutes and allowed to cool to 0-5° C. Hexane (15 mL) was added to the reaction mixture with cooling in an ice bath for 5 minutes. The fine white precepitate was collected by filtration, washed with hexane and dried to afford 8.00 g (92.2%) of the chlorosulfane derivative. A solution of ascomycin (791 mg, 1 methanol (Bundy, G. L. and Peterson. D. C. Tetrahedron Lett., 1978, 41), acetic acid: water (3:1) (Corey, E. J. and Varma. R. K. J. Am. Chem. Soc., 1971, 93, 7319), Dowex 50W-X8 in methanol (Corey, E. I., Ponder, J. W. and Ulrich, P. Tetrahedron Lett., 1980, 21, 137), boron trifluoride etherate in chloroform (Kelly, D. R., Roberts, M. S. and Newton, R. F. Synth. Commun. 1979, 9, 295), methanolic hydrogen fluoride (Hanessian, S. and Lavallee, P. Can. J. Chem., 1975, 53, 2975; ibid., 1977, 5, 562), and pyridinuim fluoride in tetrahydrofuran (Nicolaou, K. C.. Seitz, S. P., Pavia, M. R. and Petasis, N. A. J: Org. Chem., 1979, 44. 4011); pyridinium p-toluenesulfonate in ethanol (Prakash, C., Salch, S. and Blair, I. A. Tetrahedron Lett., 1989, 30, 19); N-bromosuccinimide in dimethylsulfoxide (Batten, R. J., Dixon, A. J., Taylor, R. J. K. and Newton, R. F. Synthesis, 1980, 234 ); or Tetraethyldiboroxane in the presence of catalytic amounts of trimethylsilyl triflate (Dahlhoff, W. V. and Taba, K. M. Synthesis, 1986, 561) and the like.

Workup

  1. customSynthesis, 1980, 234 )

Sources & evidence

ORD record
ord-9c16d5c2e92240c9905be934592b193e
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06121257

Reaction notes

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