Sodium Carbonate → HCID 67169347, compound

HRID 1918284Notes

Reaction equation

HRID 1918284 reaction equation
O1C2(CCCC(=O)CC2)OCC1.C(=O)([O-])[O-].[Na+].[Na+].ClC(OCC1C=CC=CC=1)=O.C(OC([NH:40][C:41]1([C:52]([OH:54])=[O:53])[CH2:51][CH2:50][CH2:49][C:44]2([O:48][CH2:47][CH2:46][O:45]2)[CH2:43][CH2:42]1)=O)C1C=CC=CC=1.C(OC(NC1(C(O)=O)CCCC(=O)CC1)=O)C1C=CC=CC=1>O1CCOCC1.O>[NH2:40][C:41]1([C:52]([OH:54])=[O:53])[CH2:51][CH2:50][CH2:49][C:44]2([O:48][CH2:47][CH2:46][O:45]2)[CH2:43][CH2:42]1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 141709101,4-dioxaspiro[4.6]undecan-8-oneHCID 67169328HCID 67169328, compoundHCID 67169855HCID 67169855, compound

Product 1

HCID 67169347HCID 67169347, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

8-Amino-1,4-dioxa-spiro[4.6]undecane-8-carboxylic acid was synthesized from 1,4-dioxa-spiro[4.6]undecan-8-one (F. Alonso et al., Tetrahedron 51 (1995), 10259-10280) via the Bucherer-Bergs route in analogy to the procedure described in J. W. Tsang et al., J. Med. Chem. 27 (1984), 1663-1668. The intermediate was suspended in dioxane/water (2.5 ml/5 ml), sodium carbonate (0.732 g, 6.90 mmol) was added, the mixture was cooled in an ice bath and benzyl chloroformate (0.392 ml, dissolved in 2.5 ml of dioxane) was added with stirring. After 4 h, the mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase was extracted with EA, the combined organic phrases were washed with water, dried over sodium sulfate and evaporated to dryness to yield a mixture of 8-benzyloxycarbonylamino-1,4-dioxa-spiro[4.6]undecane-8-carboxylic acid and 1-benzyloxycarbonylamino-4-oxo-cycloheptanecarboxylic acid.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customthe mixture was partitioned between 2 N hydrochloric acid and EA
  3. extractionthe aqueous phase was extracted with EA
  4. washthe combined organic phrases were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customto yield

Sources & evidence

ORD record
ord-506d83d4139f48f1be0d39776074f699
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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