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Lithium Hydroxide → 2-[4-Methoxy-3-(2-m-tolyl-ethylsulfanyl)-benzoylamino]-indane-2-carboxylic acid

HRID 1810879
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HRID 1810879 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[S:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.C[O:48][C:49]([C:51]1([NH2:60])[CH2:59][C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:52]1)=[O:50].[Cl-].[Li+].[OH-].[Li+]>CN(C=O)C.C1COCC1.O.CC(=O)OCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:60][C:51]2([C:49]([OH:50])=[O:48])[CH2:52][C:53]3[C:58](=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH2:59]2)=[O:9])=[CH:5][C:4]=1[S:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1
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참가 물질

10

반응물 5

HCID 3939Lithium HydroxideHCID 433294Lithium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochlorideHCID 670766864-Methoxy-3-(2-m-tolyl-ethylsulfanyl)-benzoic acid

생성물 1

HCID 44478502
2-[4-Methoxy-3-(2-m-tolyl-ethylsulfanyl)-benzoylamino]-indane-2-carboxylic acid
수율 20.8%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

700 mg of the crude compound of step 2 were dissolved in 5 ml of DMF and 598 mg (4.63 mmol) of EDIA and 968 mg (2.55 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate were added. Then a solution of 527 mg (2.32 mmol) of 2-amino-indane-2-carboxylic acid methyl ester hydrochloride in 5 ml of DMF was added. After stirring overnight, EA and an aqueous solution of lithium chloride (4%) were added, the organic phase was separated, washed once with a solution of lithium chloride and twice with a solution of sodium hydrogencarbonate, dried and evaporated. The solid residue was dissolved in 10 ml of a 9:1 mixture of THF and water, and 131 mg (5.47 mmol) of lithium hydroxide were added. After stirring overnight, the mixture was evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to give 222 mg of the title compound.

후처리

  1. customthe organic phase was separated
  2. washwashed once with a solution of lithium chloride and twice with a solution of sodium hydrogencarbonate
  3. customdried
  4. customevaporated
  5. additionwere added
  6. stirringAfter stirring overnight
  7. customthe mixture was evaporated to dryness
  8. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

출처 및 근거

ORD 기록
ord-e486fc0af8c8460b9483c345d15357af
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362073B2

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