Triethylamine → HCID 178479227, compound

HRID 1979960Notes

Reaction equation

HRID 1979960 reaction equation
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1.C(OC([NH:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]([OH:29])=[O:28])[CH2:23][CH2:22]1)=O)(C)(C)C.C(N(CC)CC)C.C(OCC)(=O)C.[ClH:43]>CN(C)C=O.C(OCC)(=O)C.CO>[ClH:43].[NH2:19][CH2:20][C@H:21]1[CH2:22][CH2:23][C@H:24]([C:27]([O:29][CH:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[O:3]2)=[O:28])[CH2:25][CH2:26]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 21866389Hydrogen chloride-ethyl acetateHCID 178453624HCID 178453624, compound

Product 1

HCID 178479227HCID 178479227, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-bromophthalide (70.5 g; 0.33 mol) in dimethylformamide (65 ml) was added dropwise to a cold solution of trans-4-(tert.-butyloxycarbonylaminomethyl) cyclohexanecarboxylic acid (77.1 g; 0.3 mol) in triethylamine (36.4 g; 0.36 mol) and dimethylformamide (195 ml). After 18 h the solvent was evaporated, water (1.5 L) and ethyl acetate (1.5 L) were added. The ethyl acetate extract was washed, dried and evaporated to give 122 g. This was dissolved in ethyl acetate (400 ml) and ethyl acetate/hydrochloric acid was added at ice bath temperature. After 2 h at room temperature, the precipitate was filtered, washed and dried to yield 63.8 g. This substance was dissolved in methanol, filtered through charcoal and precipitated with diethyl ether. Yield 54.4 g (56%), m.p. 212° C.

Workup

  1. customAfter 18 h the solvent was evaporated
  2. additionwater (1.5 L) and ethyl acetate (1.5 L) were added
  3. extractionThe ethyl acetate extract
  4. washwas washed
  5. customdried
  6. customevaporated
  7. customto give 122 g
  8. filtrationthe precipitate was filtered
  9. washwashed
  10. customdried
  11. customto yield 63.8 g
  12. filtrationfiltered through charcoal
  13. customprecipitated with diethyl ether

Sources & evidence

ORD record
ord-5719f68089394248a48c7127abdbc39f
Source dataset
uspto-grants-1984_11
Patent number
US04483867

Reaction notes

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