Chloroform → HCID 46838207, compound

HRID 1399549Notes

Reaction equation

HRID 1399549 reaction equation
C([Si]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[CH:10]\[CH3:11])(C)C)(C)(C)C.CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:41]C)C=C4)N(CC2)C1.CS(N)(=O)=O.C(Cl)(Cl)Cl>C(O)(C)(C)C.O>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:9](=[O:8])[C@H:10]([OH:41])[CH3:11])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 72879MethanesulfonamideHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 46838066HCID 46838066, compound

Product 1

HCID 46838207HCID 46838207, compound

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

Compound 10f was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-methoxyphenyl)prop-1-enyloxy)dimethylsilane, (9f, 8.1 g, 0.029 mol), AD-mix-β (40.7 g), and CH3SO2NH2 (2.8 g, 0.0294 mol) in tert-butyl alcohol-water (110 mL:110 mL) The reaction was quenched with sodium sulfite (29.1 g). After purification, 4.2 g (80%) of the desired 10f was isolated: [α]20D +71.1° (c 1.1, CHCl3); 1H NMR (CDCl3) δ 7.51-7.45 (m, 2H), 7.44-7.37 (m, 1H), 7.19-7.13 (m, 1H), 5.19-5.09 (m, 1H), 3.87 (s, 3H), 3.76 (d, 1H, J=6.5 Hz), 1.45 (d, 3H, J=7.1 Hz); 13C NMR (CDCl3) δ 202.3, 160.0, 134.7, 129.9, 121.1, 120.3, 113.1, 69.4, 55.5, 22.4. C10H12O3.

Workup

  1. customwas quenched with sodium sulfite (29.1 g)
  2. customAfter purification, 4.2 g (80%) of the
  3. customwas isolated

Sources & evidence

ORD record
ord-ac03c17086104385af8e88001a6c9148
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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