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

HRID 2406599ノート

反応式

HRID 2406599 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c1f7085fd57246de89bc426520816732
出典データセット
uspto-grants-2014_08
特許番号
US08809377B2

反応ノート

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