Ethyl Acetate → (2-(2-(2-(4-(1-(2-(Diethoxyphosphoryl)acetamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

HRID 2406599Notes

Reaction equation

HRID 2406599 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH2:13]([O:15][P:16]([CH2:21][C:22]([OH:24])=O)([O:18][CH2:19][CH3:20])=[O:17])[CH3:14].[NH2:25][CH:26]([C:30]1[CH:59]=[CH:58][C:33]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][N:43]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:32][CH:31]=1)[CH2:27][CH2:28][CH3:29].C(OCC)(=O)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:19]([O:18][P:16]([CH2:21][C:22]([NH:25][CH:26]([C:30]1[CH:31]=[CH:32][C:33]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][N:43]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])=[CH:58][CH:59]=1)[CH2:27][CH2:28][CH3:29])=[O:24])([O:15][CH2:13][CH3:14])=[O:17])[CH3:20]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 36704(Diethoxyphosphinyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68041434(2-(2-(2-(4-(1-Aminobutyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

Product 1

HCID 86762604(2-(2-(2-(4-(1-(2-(Diethoxyphosphoryl)acetamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl esterYield 99.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-dimethylaminopyridine (DMAP; 197 mg, 1.61 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl; 309 mg, 1.61 mmol) was added to a stirred solution of diethylphosphonoacetic acid (129 μL, 0.805 mmol) and (2-(2-(2-(4-(1-aminobutyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester (45; 400 mg, 0.805 mmol) in N,N-dimethylformamide (10 mL). The resulting mixture was stirred under nitrogen for 3 hours at room temperature, and then poured into 100 mL of ethyl acetate. This solution was washed with 1N aqueous HCl (2×) and sat. brine, dried over sodium sulfate, and concentrated to an oil. Purification by flash silica gel column chromatography, eluting with ethyl acetate, afforded 49 (540 mg, quantitative) as a clear oil: MS (ES+) m/z 675.3 (M+H)+.

Workup

  1. washThis solution was washed with 1N aqueous HCl (2×) and sat. brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to an oil
  4. customPurification by flash silica gel column chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c1f7085fd57246de89bc426520816732
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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