تفاعل #340189

ord-2d9fc3b66bd44134a3d2dec12d6c8e9b

معادلة التفاعل

O=C(O)c1ccc(Br)cc1
4-bromobenzoic acid
On1nnc2ccccc21
1-hydroxybenzotriazole
CCN=C=NCCCN(C)C.Cl
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
O=C([O-])O.[Na+]
sodium hydrogencarbonate
O=C([O-])[O-].[K+].[K+]
Potassium carbonate
CC[C@H]1COCCN1S(=O)(=O)c1ccccc1[N+](=O)[O-]
title compound
CC[C@H]1COCCN1S(=O)(=O)c1ccccc1[N+](=O)[O-]
(S)-3-Ethyl-4-(2-nitrophenylsulfonyl)morpholine
Sc1ccc(Br)cc1
4-Bromobenzenethiol
CC[C@H]1COCCN1C(=O)c1ccc(Br)cc1
title compound
المردود 72.0%
CC[C@H]1COCCN1C(=O)c1ccc(Br)cc1
(S)-(4-Bromophenyl)(3-ethylmorpholino)methanone
المردود 72.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGthe mixture was stirred at room temperature for 5 hr
  2. 2
    workup.STIRRINGthe mixture was stirred at room temperature for 4.5 hr
  3. 3
    أخرىthe reaction
  4. 4
    استخلاصfollowed by extraction with ethyl acetate
  5. 5
    تجفيفThe extract was dried over anhydrous sodium sulfate
  6. 6
    ترشيحwas then filtered
  7. 7
    تركيزThe filtrate was concentrated under the reduced pressure
  8. 8
    أخرىwas then purified by preparative thin layer chromatography (hexane:ethyl acetate=1:4)

الإجراء التجريبي

Potassium carbonate (49.1 mg, 0.355 mmol) was added to a solution of 89 mg (0.296 mmol) of the title compound produced in step (iii) of Reference Example 9 in N,N-dimethylformamide (1.0 ml), and the mixture was stirred at room temperature for 5 min. 4-Bromobenzenethiol (56.0 mg, 0.296 mmol) was added thereto, and the mixture was stirred at room temperature for 5 hr. Thereafter, N,N-dimethylformamide (1.0 ml), 119.0 mg (0.592 mmol) of 4-bromobenzoic acid, 80.0 mg (0.592 mmol) of 1-hydroxybenzotriazole, and 119.0 mg (0.592 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were successively added thereto, and the mixture was stirred at room temperature for 4.5 hr. A saturated aqueous sodium hydrogencarbonate solution was added thereto to stop the reaction, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure and was then purified by preparative thin layer chromatography (hexane:ethyl acetate=1:4) to give 64 mg (2 steps, yield 72%) of the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07871982B2uspto-grants-2011_01