Ethyl Acetate → HCID 9874234, compound

HRID 1684624Notes

Reaction equation

HRID 1684624 reaction equation
[F:1][C:2]1[C:3]([F:43])=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[O:18][C:17]([CH3:23])([CH3:22])[CH:16]([CH2:24][C:25]3[CH:26]=[C:27]([NH:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])[CH:28]=[CH:29][C:30]=3[O:31][CH3:32])[C:15]4=[O:41])=[N:7][C:6]=2[CH:42]=1.C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[C:3]([F:43])=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[O:18][C:17]([CH3:23])([CH3:22])[C@@H:16]([CH2:24][C:25]3[CH:26]=[C:27]([NH:33][S:34]([C:37]([F:38])([F:39])[F:40])(=[O:35])=[O:36])[CH:28]=[CH:29][C:30]=3[O:31][CH3:32])[C@H:15]4[OH:41])=[N:7][C:6]=2[CH:42]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 67717279HCID 67717279, compound

Product 1

HCID 9874234HCID 9874234, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1.36 g (2.12 mole) of the product of Example 104 in 20 mL tetrahydrofuran at -78° C. was added dropwise 4.7 mL (4.66 mL) 1.0M LiB(C2H5)3H in THF (Super-Hydride [trademark]). The mixture was allowed to come to room temperature over 3 hours, then quenched with 10 mL 10% ammonium chloride. The mixture was poured into water, acidified to ph 1-4 with 1N HCl and then extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 30% ethyl acetate in hexanes gave 670 mg (48%) of pure product. NMR (CDCl3): δ1.40 (s, 3H); 1.53 (s, 3H); 2.10 (m, 1H); 2.90 (m, 2H); 3.88 (s, 3H); 4.23 (s, br, 1H); 5.29 (s, 2H). MS (LSIMS) m/e: 644 (M+, 12), 627 (32), 268 (100).

Workup

  1. customquenched with 10 mL 10% ammonium chloride
  2. additionThe mixture was poured into water
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oil

Sources & evidence

ORD record
ord-8f22b25cd7fe4097bd828f76b843ab2d
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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