Glycine ethyl ester → HCID 66650621, compound

HRID 417808Notes

Reaction equation

HRID 417808 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([P:8]([N:24]([CH2:28][CH2:29][Cl:30])[CH2:25][CH2:26][Cl:27])([O:10][CH2:11][CH2:12][S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=1)=[O:9])[CH2:5][CH2:6][Cl:7].C(N(C(C)C)CC)(C)C.[CH2:40]([O:42][C:43](=[O:46])[CH2:44][NH2:45])[CH3:41].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.CN(C)C=O>[Cl:27][CH2:26][CH2:25][N:24]([P:8]([N:4]([CH2:3][CH2:2][Cl:1])[CH2:5][CH2:6][Cl:7])([O:10][CH2:11][CH2:12][S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:45][CH2:44][C:43]([O:42][CH2:40][CH3:41])=[O:46])=[O:22])=[CH:17][CH:16]=1)=[O:9])[CH2:28][CH2:29][Cl:30]

Participants

7

Reactant 4

HCID 12176Glycine ethyl esterHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66650850alpha-[[2-[[Bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]-4-carboxytoluene

Product 1

HCID 66650621HCID 66650621, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To α-[[2-[[Bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]-4-carboxytoluene, 411 mg, in 10 mL dichloromethane was added 400 μL diisopropylethylamine and glycine ethyl ester, 212 mg. The solution was cooled to 0° C. and HBTU, 317 mg, in 2 mL dimethylformamide was added, after which the mixture was allowed to warm to room temperature. The reaction mixture was diluted with dichloromethane, then washed 3 times with 1 M hydrochloric acid, 5 times with saturated aqueous sodium bicarbonate, and once with brine. The organic layer was dried over MgSO4, filtered, and the solvents removed under vacuum to give α-[[2-[[bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]-4-[(ethoxycarbonylmethyl)aminocarbonyl]toluene as a clear oil, 411 mg, with product identity verified by LC-MS.

Workup

  1. temperatureto warm to room temperature
  2. washwashed 3 times with 1 M hydrochloric acid, 5 times with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-24bc22cfd6a64c3b990c58cfc7f5c751
Source dataset
uspto-grants-2012_01
Patent number
US08093231B2

Reaction notes

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