Diisopropylethylamine → HCID 23560783, compound

HRID 1058413Notes

Reaction equation

HRID 1058413 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[OH:25][C:26]1[CH:27]=[C:28]([CH:43]=[CH:44][CH:45]=1)[CH2:29][NH:30][C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=O)=[C:35]([CH3:42])[CH:34]=1)=[O:32].[CH3:46][O:47][C:48](=[O:57])[CH:49]([P:51]([O:55][CH3:56])([O:53][CH3:54])=[O:52])[NH2:50].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:46][O:47][C:48](=[O:57])[CH:49]([P:51]([O:53][CH3:54])([O:55][CH3:56])=[O:52])[NH:50][C:37](=[O:39])[C:36]1[CH:40]=[CH:41][C:33]([C:31]([NH:30][CH2:29][C:28]2[CH:43]=[CH:44][CH:45]=[C:26]([OH:25])[CH:27]=2)=[O:32])=[CH:34][C:35]=1[CH3:42]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11084793Methyl 2-amino-2-(dimethoxyphosphoryl)acetateHCID 22661302HCID 22661302, compound

Product 1

HCID 23560783HCID 23560783, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (3.50 g, 9.2 mmol) was added to a solution of 4-[[(3-hydroxybenzyl)amino]carbonyl]-2-methylbenzoic acid (Example 90; 2.40 g, 8.4 mmol), rac.-2-(dimethoxyphosphinyl)glycine methyl ester (Example 125; 1.80 g, 9.1 mmol) and diisopropylethylamine (1.50 g, 11.6 mmol) in N,N-dimethylformamide (50 mL). The solution was stirred overnight at room temperature. Ethyl acetate (200 mL) was added and the solution was washed with 1N hydrochloric acid solution, water and brine (200 mL each), dried (MgSO4), filtered and evaporated to give crude rac.-2-(dimethoxyphosphinyl)-N-[4-[[(3-hydroxybenzyl)amino]carbonyl]-2-methylbenzoyl]glycine methyl ester (2.47 g, 63% yield). This material was used in subsequent reactions without flrther purification.

Workup

  1. washthe solution was washed with 1N hydrochloric acid solution, water and brine (200 mL each)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1a1c49666fa64e72bc62c746a701a3d5
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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