Triethylamine → alpha-(tert-Butoxycarbonyl)amino(2,3-dihydro-5-benzofuranyl)acetic acid

HRID 904019Notes

Reaction equation

HRID 904019 reaction equation
[NH2:1][CH:2]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)[C:3]([OH:5])=[O:4].O1CCOCC1.O.C(N(CC)CC)C.[C:29]([O:33][C:34](N=[N+]=[N-])=[O:35])([CH3:32])([CH3:31])[CH3:30]>O>[C:29]([O:33][C:34]([C:2]([NH2:1])([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)[C:3]([OH:5])=[O:4])=[O:35])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 205312232-Amino-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acidHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 86736284alpha-(tert-Butoxycarbonyl)amino(2,3-dihydro-5-benzofuranyl)acetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

α-Amino(2,3-dihydro-5-benzofuranyl)acetic acid (192 mg, 1 mmole) is added to 10 ml of 1:1 dioxane-water mixture with 4 mM of triethylamine and 0.17 ml of tert-butoxycarbonylazide. This mixture is stirred overnight at room temperature. The mixture is diluted with water and extracted with chloroform. The chloroform is dried and evaporated. The residue is taken up in ethyl acetate and washed with dilute aqueous hydrochloric acid. The organic layer is dried over magnesium sulfate and evaporated to give the title compound in a yield of about 80%.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe chloroform is dried
  3. customevaporated
  4. washwashed with dilute aqueous hydrochloric acid
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-3b67a053f50242c8b3e1b1c657227f2b
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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