Benzyloxycarbonylglycine → HCID 70043751, compound

HRID 487421Notes

Reaction equation

HRID 487421 reaction equation
[ClH:1].[C:2]([O:6][C:7](=[O:24])[CH2:8][N:9]1[CH2:14][CH2:13][NH:12][C@@H:11]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]1=[O:23])([CH3:5])([CH3:4])[CH3:3].C(OC([NH:35][CH2:36][C:37](O)=[O:38])=O)C1C=CC=CC=1.C(P(=O)(OCC)OCC)#N.Cl.O1CCOCC1>CO.[C].[Pd].C(N(CC)CC)C.CN(C)C=O>[ClH:1].[C:2]([O:6][C:7](=[O:24])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:37](=[O:38])[CH2:36][NH2:35])[C@@H:11]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]1=[O:23])([CH3:4])([CH3:3])[CH3:5]

Participants

9

Reactant 4

HCID 14349BenzyloxycarbonylglycineHCID 76257Diethyl cyanophosphonateHCID 204431481,4-Dioxane hydrochlorideHCID 70043966HCID 70043966, compound

Product 1

HCID 70043751HCID 70043751, compoundYield 60.8%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3.7 g of (S)-2-oxopiperazine-1,3-diacetic acid di-t-butyl ester hydrochloride, 3.3 g of N-benzyloxycarbonyl glycine and 10 ml of dimethylformamide were added dropwise, while stirring at 0° C., 3.1 g of diethyl cyanophosphonate then 3.2 g of triethylamine in the course of 10 minutes. The mixture was stirred for one hour at the same temperature then for 3 hours at room temperature. The reaction mixture was poured into ice-water, which was subjected to extraction with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate and concentrated to give a crude product. The crude product was dissolved in 30 ml of methanol, to which were added 1 g of 10% palladium-carbon and 1.8 ml of 4N HCl-dioxane solution. The mixture was stirred for one hour at room temperature under hydrogen. The catalyst was removed, and the reaction mixture was concentrated under reduced pressure to afford 2.6 g of the title compound as a colorless oily product. This product was processed with ether to give colorless powder.

Workup

  1. additionwere added dropwise
  2. customin the course of 10 minutes
  3. stirringThe mixture was stirred for one hour at the same temperature
  4. extractionwas subjected to extraction with ethyl acetate
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude product
  8. stirringThe mixture was stirred for one hour at room temperature under hydrogen
  9. customThe catalyst was removed
  10. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-451a2812f81045bcaf4734c10b42413d
Source dataset
uspto-grants-1994_03
Patent number
US05294713

Reaction notes

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