HCID 90889006, compound → HCID 68998531, compound

HRID 1984569Notes

Reaction equation

HRID 1984569 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([S:11]([C:14]3[S:18][C:17]([CH2:19][NH:20][C:21]([C:23]4[C:24](=[O:29])[NH:25][CH:26]=[CH:27][CH:28]=4)=[O:22])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH2:7][CH2:6]2)[O:4]CC1>CC(C)=O.Cl.C=O>[O:29]=[C:24]1[C:23]([C:21]([NH:20][CH2:19][C:17]2[S:18][C:14]([S:11]([N:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)(=[O:13])=[O:12])=[CH:15][CH:16]=2)=[O:22])=[CH:28][CH:27]=[CH:26][NH:25]1

Participants

5

Reactant 1

HCID 90889006HCID 90889006, compound

Product 1

HCID 68998531HCID 68998531, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 712FormaldehydeSolvent

Procedure

A solution of the ketal 198a (6.0 g, 13.7 mmol) in acetone (60 ml), HCl aq. 1N (30 ml) and conc. aq. formaldehyde (8 ml) was heated to 48° C. for 15 h. The mixture was concentrated to a total weight of 46 g, whereupon an orange oil separated out, and CH2Cl2 was added (200 ml). The orange oil went in the organic phase, while water (27 ml) separated out and was removed. The CH2Cl2 layer was rinsed with a small amount of water (20 ml), dried (MgSO4), and concentrated to afforded the crude ketone as hemiaminal (5.1 g, 88%).

Workup

  1. concentrationThe mixture was concentrated to a total weight of 46 g, whereupon an orange oil
  2. customseparated out
  3. additionCH2Cl2 was added (200 ml)
  4. customseparated out
  5. customwas removed
  6. washThe CH2Cl2 layer was rinsed with a small amount of water (20 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-64f5b1cd279642aba9645a898d840507
Source dataset
uspto-grants-2009_06
Patent number
US07544700B2

Reaction notes

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