Triethylamine → HCID 20372098, compound

HRID 1834797Notes

Reaction equation

HRID 1834797 reaction equation
[NH2:1][CH:2]([C:6]1[O:7][CH2:8][CH2:9][S:10][CH:11]=1)[C:3]([OH:5])=[O:4].[C:12]([O:16][C:17](N=[N+]=[N-])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C)C=O>[C:12]([O:16][C:17]([NH:1][CH:2]([C:6]1[O:7][CH2:8][CH2:9][S:10][CH:11]=1)[C:3]([OH:5])=[O:4])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 20372082HCID 20372082, compound

Product 1

HCID 20372098HCID 20372098, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

DL-α-Amino-(5,6-dihydro-1,4-oxathiin-2-yl)-acetic acid (25.4 g.) is suspended in dimethylformamide (435 cc.); tert.-butoxycarbonyl azide (41.5 g.) and triethylamine (51 cc.) are added. The reagents are left in contact for 48 hours whilst stirring at a temperature of 35° C. The solution is concentrated under reduced pressure (1 mm Hg), the residue is taken up in water (300 cc.), and the pH is adjusted to 8.5 by adding a saturated sodium bicarbonate solution. The aqueous phase is extracted twice with ethyl ether (a total of 500 cc.) which is discarded, and is then acidified to pH = 3 by adding 4 N hydrochloric acid A product precipitates, which is filtered off and then dissolved in methylene chloride (600 cc.). The solution obtained is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg). DL-α-Tert.-butoxycarbonylamino-(5,6-dihydro-1,4-oxathiin-2-yl)-acetic acid (26.2 g.), melting at 160° C is thus obtained.

Workup

  1. concentrationThe solution is concentrated under reduced pressure (1 mm Hg)
  2. additionby adding a saturated sodium bicarbonate solution
  3. extractionThe aqueous phase is extracted twice with ethyl ether (a total of 500 cc
  4. additionby adding 4 N hydrochloric acid A product
  5. customprecipitates
  6. filtrationwhich is filtered off
  7. dissolutiondissolved in methylene chloride (600 cc.)
  8. customThe solution obtained
  9. dry with materialis dried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)

Sources & evidence

ORD record
ord-2dfa9a8e799c40358c70aceb19182541
Source dataset
uspto-grants-1978_01
Patent number
US04071531

Reaction notes

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