(Diethoxyphosphinyl)acetic acid → HCID 86702812, compound

HRID 1850046Notes

Reaction equation

HRID 1850046 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].[CH2:25]([O:27][P:28]([CH2:33][C:34](O)=[O:35])([O:30][CH2:31][CH3:32])=[O:29])[CH3:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:31]([O:30][P:28]([CH2:33][C:34]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:35])([O:27][CH2:25][CH3:26])=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 36704(Diethoxyphosphinyl)acetic acidHCID 81531DiisopropylethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86702812HCID 86702812, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (5.16 g, 6.90 mL, 40 mmol) and tert-butyl 2-aminophenylcarbamate (2.08 g, 10 mmol) were added to a solution of 2-(diethoxyphosphoryl)acetic acid (2.15 g, 11 mmol) in DCM (120 mL). After the mixture was stirred for ten minutes, HATU (4.56 g, 12 mmol) was added to the reaction and stirring was prolonged for 6 h at room temperature under a nitrogen atmosphere. After completion of the reaction as indicated by HPLC, the reaction mixture was washed with saturated NaHCO3 and brine. It was dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo to get the crude product, which was triturated with 30% v/v hexanes in EtOAc for 30 min. The solid was filtered, washed with 30% hexanes in EtOAc and dried to get 2.92 g of tert-butyl (2-(2-(diethoxyphosphoryl)acetamido)phenyl)carbamate as an off-white solid in 76% yield.

Workup

  1. stirringstirring
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed with saturated NaHCO3 and brine
  4. dry with materialIt was dried over Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customto get the crude product, which
  8. customwas triturated with 30% v/v hexanes in EtOAc for 30 min
  9. filtrationThe solid was filtered
  10. washwashed with 30% hexanes in EtOAc
  11. customdried

Sources & evidence

ORD record
ord-3b1657889f7d4530adc038e6f76beb18
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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