1-Hydroxybenzotriazole → 2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino)carbonyl]benzoic acid, methyl ester

HRID 393032

반응식

HRID 393032 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O-:10])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[C:16]1([C@H:26]([NH2:28])[CH3:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:11][C:4]1[CH:5]=[C:6]([C:8]([NH:28][C@@H:26]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH3:27])=[O:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 857711412,6-Dichlorobenzene-1,4-dicarboxylic acid, 1-methyl ester

생성물 1

HCID 865851452,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino)carbonyl]benzoic acid, methyl ester수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2,6-dichlorobenzene-1,4-dicarboxylic acid, 1-methyl ester (Example 4; 3.00 g, 12.0 mmol), (R)-(+)-1-(1-naphthyl)ethylamine (2.00 g, 11.7 mmol), HBTU (5.68 g, 15.0 mmol), HOBT (2.04 g, 15.1 mmol), and diisopropylethylamine (6.20 g, 48.0 mmol) in N,N-dimethylformamide (50 mL) was stirred at room temperature over the weekend. The solvent was evaporated and ethyl acetate (150 mL) was added. The solution was washed with 1 M HCl (100 mL) and the aqueous layer was back-extracted with ethyl, acetate (100 mL). The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate and brine (200 mL each), then dried (MgSO4), filtered, evaporated and chromatographed (30% ethyl acetate/hexanes) to give 2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoic acid, methyl ester (4.52 g, 96%) as a white foam.

후처리

  1. customThe solvent was evaporated
  2. additionethyl acetate (150 mL) was added
  3. washThe solution was washed with 1 M HCl (100 mL)
  4. extractionthe aqueous layer was back-extracted with ethyl, acetate (100 mL)
  5. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate and brine (200 mL each)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed (30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-c939f1f15fa5473a8d2b7ba0072986b0
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803384B2

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