Sodium Hydroxide → HCID 44248859, 화합물

HRID 1441907

반응식

HRID 1441907 반응식
Cl.[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6][SH:7])[CH3:3].[OH-].[Na+].[Cl:12][CH2:13][CH2:14][N:15]([CH2:39][CH2:40][Cl:41])[P:16]([N:32]([CH2:36][CH2:37][Cl:38])[CH2:33][CH2:34][Cl:35])(=[O:31])[O:17][CH2:18][CH2:19]OS(C1C=CC(Br)=CC=1)(=O)=O>CO>[Cl:41][CH2:40][CH2:39][N:15]([CH2:14][CH2:13][Cl:12])[P:16]([N:32]([CH2:36][CH2:37][Cl:38])[CH2:33][CH2:34][Cl:35])(=[O:31])[O:17][CH2:18][CH2:19][S:7][CH2:6][CH2:5][N:4]([CH2:8][CH3:9])[CH2:2][CH3:3]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 16031Ethanethiol, 2-(diethylamino)-, hydrochloride (1:1)HCID 17949377HCID 17949377, 화합물2회

생성물 1

HCID 44248859HCID 44248859, 화합물수율 42.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2-(diethylamino)ethanethiol hydrochloride (840 g, 5 mmol) in methanol (20 mL) was added NaOH (3.8 mL of 4M solution in methanol, 15 mmol, 3 eq.) and 2-(4-bromobenzenesulfonyloxy)ethyl N,N,N′,N′-tetrakis(2-chloroethyl)phosphorodiamidate (7.0 mL of 0.7M solution in toluene, 4.9 mmol, 0.98 eq.). The mixture was stirred at room temperature until all the 2-(4-bromobenzenesulfonyloxy)ethyl N,N,N′,N′-tetrakis(2-chloroethyl)phosphorodiamidate was consumed, as determined by HPLC-ELSD. The mixture was acidified to pH 7 with 1.0 M aqueous H3PO4 and concentrated under vacuum to a thick slurry. The slurry was taken up in ethyl acetate (400 mL) and washed with 5% aqueous NaHCO3 (2×400 mL) and then with aqueous HCl (2×400 mL). The acidic aqueous layers were combined and brought to pH>9 with solid NaHCO3, then extracted with ethyl acetate (2×800 mL). The ethyl acetate solution was separated, dried over anhydrous MgSO4, filtered, and concentrated under vacuum to give 2-{[2-(diethylamino)ethyl]thio}ethyl N,N,N′,N′-tetrakis(2-chloroethyl)phosphorodiamidate as a clear oil (1.05 g, 42% yield). The 2-{[2-(diethylamino)ethyl]thio}ethyl N,N,N′,N′-tetrakis(2-chloroethyl)phosphorodiamidate was oxidized to 2-{[2-(diethylamino)ethyl]sulfonyl}ethyl N,N,N′,N′-tetrakis(2-chloroethyl)phosphorodiamidate and isolated as the hydrochloride salt using the procedure of Synthetic Example 1. MS (ES+): m/z=536 [C16H35Cl4N3O4PS+H]; 1H NMR (CD3OD): δ=1.36 (t, J=7.4 Hz, 6H), 3.28-3.34 (m, 2H), 3.40-3.50 (m, 10H), 3.65-3.77 (m, 14H), 4.51 (dd, J=5.1, 6.3 Hz, 2H); 31P NMR (CD3OD): δ=18.02.

후처리

  1. customwas consumed
  2. concentrationconcentrated under vacuum to a thick slurry
  3. washwashed with 5% aqueous NaHCO3 (2×400 mL)
  4. extractionextracted with ethyl acetate (2×800 mL)
  5. customThe ethyl acetate solution was separated
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-76c19d8267ef41649a76026aca5cc64a
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655799B2

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