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Triethylamine → (+/-)-[[[2,6-Bis(1-methylethyl)phenyl]amino]2-oxoethyl]-(phenylmethyl)phosphoramidic Acid, Nonyl Phenyl Ester

HRID 247828
Notes
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Reaction equation

HRID 247828 reaction equation
[P:1](Cl)(Cl)([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:2].C(N(CC)CC)C.[CH2:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH3:29][CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:33]=1[NH:41][C:42](=[O:52])[CH2:43][NH:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH3:31]>C1(C)C=CC=CC=1>[CH3:31][CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:39])[CH3:40])[C:33]=1[NH:41][C:42](=[O:52])[CH2:43][N:44]([CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[P:1](=[O:2])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:28][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 89141-NonanolHCID 13038Phosphorodichloridic acid, phenyl esterHCID 19764427N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamide

Product 1

HCID 86746783(+/-)-[[[2,6-Bis(1-methylethyl)phenyl]amino]2-oxoethyl]-(phenylmethyl)phosphoramidic Acid, Nonyl Phenyl EsterYield 31.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To an ice-cooled solution of phenyl dichlorophosphate (2.83 g, 0.02 mol) in dry toluene (50 mL) is added triethylamine (2.02 g, 0.02 mol) followed by nonyl alcohol (2.89 g, 0.02 mol) in dry toluene (40 mL) dropwise. The reaction mixture is stirred in an ice bath for 2 hours and then filtered. To this filtrate are added triethylamine (2.02 g, 0.02 mol) and a solution of N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamide (Example V) (6.40 g, 0.02 mole) and the mixture is stirred at room temperature overnight. The reaction mixture is filtered and concentrated. Flash column chromatography and crystallization from ethyl acetate affords 3.8 g of the title compound; IR (KBr); 3285, 2961, 2925, 2858, 2367, 1684, and 1508. 1H NMR (250 MHz, DMSO)δ9.22 (1 H, s), 7.44-6.92 (13 H, m), 4.50-4.30 (2 H, m), 4.30-4.00 (2 H, m), 4.00-3.60 (2 H, m), 3.10-2.80 (2 H, m), 1.70-1.40 (2 H, m), 1.4-1.18 (12 H, m), 1.18-1.00 (12 H, d, J=7 Hz), 0.98-0.76 (3 H, m).

Workup

  1. filtrationfiltered
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated
  4. customFlash column chromatography and crystallization from ethyl acetate

Sources & evidence

ORD record
ord-4686ccefd43947c99c2937b26ae79b6f
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05208224

Reaction notes

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