Hydrochloric Acid → HCID 70049889, compound

HRID 1683958Notes

Reaction equation

HRID 1683958 reaction equation
Cl.N[C@@H:3]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:4]([NH:6][C@@H:7]([CH2:18][CH2:19][CH2:20][CH3:21])[C:8](=[O:17])[CH2:9][S:10][CH2:11][C:12]1[O:16][CH:15]=[CH:14][CH:13]=1)=[O:5].[O:26]([CH2:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([N:39](CC)CC)C.Cl>C(Cl)Cl>[CH2:11]([S:10][CH2:9][C:8](=[O:17])[C@@H:7]([NH:6][C:4](=[O:5])[CH2:3][CH2:22][C@H:23]([CH3:25])[CH2:24][NH:39][C:34](=[O:35])[CH2:33][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:18][CH2:19][CH2:20][CH3:21])[C:12]1[O:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 70049849HCID 70049849, compound

Product 1

HCID 70049889HCID 70049889, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(s)-3-((s)-2-Amino-4-methylvalerylamino)-1-furfurylthio-2-heptanone hydrochloride (4.31 g) obtained in Example 2 was dissolved in methylene chloride (100 ml) and chilled to 0° C. To the solution were added phenoxyacetylchloride (2.07 g) and triethylamine (3.2 ml), and the mixture was stirred at 0° C. for 30 minutes, and at room temperature for 30 minutes. Then, 0.5N aqueous hydrochloric acid (50 ml) was added to the mixture, which was extracted with methylene chloride. The extract was washed with water, saturated sodium hydrogencarbonate and saturated brine sequentially, dried over magnesium sulfate and filtered. The filtrate was concentrated, and chromatographed on a silica gel column, eluting with hexane containing 25% ethyl acetate to give the titled product (3.96 g).

Workup

  1. waitat room temperature for 30 minutes
  2. extractionwas extracted with methylene chloride
  3. washThe extract was washed with water, saturated sodium hydrogencarbonate and saturated brine sequentially
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customchromatographed on a silica gel column
  8. washeluting with hexane containing 25% ethyl acetate

Sources & evidence

ORD record
ord-b3994c1fbc8240e190d04854a6d0dfb9
Source dataset
uspto-grants-1997_06
Patent number
US05639783

Reaction notes

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