Dicyclohexylcarbodiimide → HCID 76501932, compound

HRID 2165270Notes

Reaction equation

HRID 2165270 reaction equation
C(O[C:9]([NH:11][C@H:12]1[CH2:15][N:14]([O:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]1=[O:25])=[O:10])C1C=CC=CC=1.[NH2:26][C:27]1[S:28][CH:29]=[C:30](/[C:32](=[N:36]/[O:37][CH3:38])/C(O)=O)[N:31]=1.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.[Pd]>[NH2:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:36][O:37][CH3:38])[C:9]([NH:11][CH:12]2[CH2:15][N:14]([O:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C:13]2=[O:25])=[O:10])[N:31]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 86744079HCID 86744079, compound

Product 1

HCID 76501932HCID 76501932, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×

Procedure

(S)-[[3-[(Benzyloxycarbonyl)amino]-2-oxo1-azetidinyl]oxy]acetic acid. 1,1-dimethylethyl ester (1.4 g, 4.0 mmol) was dissolved in 25 ml of dry dimethylformamide and hydrogenated with 1 g of 10% palladium on charcoal as catalyst. After 20 minutes the catalyst was filtered and a mixture of (Z)-2-amino-α-(methoxyimino)-4-thiazoleacetic acid (4.4 mmol). 1-hydroxybenzotriazole hydrate (0.15 g, 1.0 mmol). dicyclohexylcarbodiimide (0.81g. 4.4 mmol) and 30 ml of dry dimethylformamide was added. The mixture was stirred overnight at room temperature. The precipitated dicyclohexyl urea was filtered off and the solvent removed in vacuo. The residue was dissolved in ethyl acetate, washed with 5% NaHCO3 and dried over MgSO4. Filtration and evaporation in vacuo gave the title compound which solidified by stirring with ether/petroleum ether; melting point 120° C. dec.

Workup

  1. filtrationAfter 20 minutes the catalyst was filtered
  2. filtrationThe precipitated dicyclohexyl urea was filtered off
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 5% NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and evaporation in vacuo

Sources & evidence

ORD record
ord-28a1ba906fad479a99bd6dd50721c93a
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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