Sodium Chloride → N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-4-chloromandelamide

HRID 1614752

반응식

HRID 1614752 반응식
Br.[NH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([OH:13])=[CH:8][CH:9]=2)[CH2:4]1.[Cl:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]([OH:23])[C:20](O)=[O:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.[Cl-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[OH:13][C:7]1[CH:6]=[C:5]2[C:10]([CH2:11][CH2:12][CH:3]([NH:2][C:20](=[O:21])[CH:19]([C:18]3[CH:24]=[CH:25][C:15]([Cl:14])=[CH:16][CH:17]=3)[OH:23])[CH2:4]2)=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 102994-Chloromandelic acidHCID 147509162-Amino-7-hydroxytetralin hydrobromide

생성물 1

HCID 19745537N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-4-chloromandelamide수율 63.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 3.2 g of 2-amino-7-hydroxytetralin hydrobromide (PREPARATION Ic), 2.4 g of 4-chloromandelic acid and 5.2 g of benzotriazolyl-N-oxytris-(dimethylamino) phosphonium hexafluorophosphate in 50 ml of methylene chloride, there is added 3.6 ml of triethylamine. The solution obtained is left under stirring at room temperature for 3 hours, then a saturated sodium chloride solution is added and the mixture is stirred for 30 minutes. The organic phase that separates is evaporated to dryness and an oil is obtained that is dissolved in 200 ml of ethyl acetate. The solution thus obtained is washed twice with 40 ml of a 2N hydrochloric acid, twice with a saturated sodium bicarbonate solution and, then, with a saturated sodium chloride solution. The solution is dried over sodium sulfate, filtered and evaporated to dryness. The oil so obtained is chromatographed (elution with a 1/1 mixture of ethyl acetate/cyclohexane) and all of the fractions are collected. An amount of 2.7 g (63%) of N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-4-chloromandelamide is obtained as a diastereoisomeric mixture; m.p. about 170° C. (large interval of melting), pure enough for a further reaction. In this mixture, the (RS,SR) and (RR,SS) diastereoisomers are well detectable by chromatography; they are easily separable and obtainable in pure form.

후처리

  1. customThe solution obtained
  2. waitis left
  3. stirringthe mixture is stirred for 30 minutes
  4. customThe organic phase that separates is evaporated to dryness
  5. customan oil is obtained
  6. customThe solution thus obtained
  7. washis washed twice with 40 ml of a 2N hydrochloric acid, twice with a saturated sodium bicarbonate solution
  8. dry with materialThe solution is dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe oil so obtained
  12. customis chromatographed (
  13. washelution
  14. additionwith a 1/1 mixture of ethyl acetate/cyclohexane) and all of the fractions
  15. customare collected

출처 및 근거

ORD 기록
ord-da7e7e88fc374baeb96c27881761e819
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198586

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