Dimethylformamide → HCID 22850968, compound

HRID 487422Notes

Reaction equation

HRID 487422 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][NH:8][CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:25][C:26]([NH:28][C@H:29]([C:37](O)=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)C=O.C(P(=O)(OCC)OCC)#N>C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:17])[CH2:7][N:8]([C:37](=[O:38])[C@H:29]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[NH:28][C:26]([O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:27])[CH2:9][CH:10]([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 76257Diethyl cyanophosphonateHCID 19094644HCID 19094644, compound

Product 1

HCID 22850968HCID 22850968, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 11.0 g of N-(2,2-diethoxyethyl)glycine t-butyl ester, 13.3 g of N-benzyloxycarbonyl-L-phenylalanine and 50 ml of dimethylformamide was cooled to 0° C., and there were added dropwise 9.4 g of diethyl cyanophosphonate, then 5.9 g of triethylamine. The mixture was stirred for one hour at the same temperature, then for 5 hours at room temperature. The reaction mixture was diluted with ethyl acetate, which was poured into ice-water. The ethyl acetate layer was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure to give a crude product. The crude product was purified by means of chromatography on silica gel using an eluent (n-hexane:ethyl acetate=9:1) to afford 20.0 g of the title compound as a colorless oily product.

Workup

  1. waitfor 5 hours at room temperature
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThe crude product was purified by means of chromatography on silica gel using an eluent (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-a7343994d324410380ed86f7e7007540
Source dataset
uspto-grants-1994_03
Patent number
US05294713

Reaction notes

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