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Acetic Acid → 4-{[(2,4-Dichloro-thiazol-5-yl)methyl]-isobutyl-amino}-piperidine-1-carboxylic acid t-butyl ester

HRID 2111898
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HRID 2111898 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[S:21][C:22]([CH:26]=O)=[C:23]([Cl:25])[N:24]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:26][C:22]2[S:21][C:20]([Cl:19])=[N:24][C:23]=2[Cl:25])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 15380699tert-Butyl 4-(isobutylamino)piperidine-1-carboxylate

생성물 1

HCID 685764924-{[(2,4-Dichloro-thiazol-5-yl)methyl]-isobutyl-amino}-piperidine-1-carboxylic acid t-butyl ester수율 31.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(isobutylamino)-piperidine-1-carboxylic acid tert-butyl ester (797 mg, 2.28 mmol, 1 eq.) and 2,4-dichloro-5-thiazolecarboxaldehyde (500 mg, 2.75 mmol, 1.2 eq) in anhydrous dimethylformamide (10 ml), is added glacial acetic acid (130 uL, 2.28 mmol, 1 eq.) and NaBH(OAc)3 (677 mg, 3.19 mmol, 1.4 eq.). The reaction mixture is stirred at room temperature for 3 days and then water and ethyl acetate are added. The layers are separated and the aqueous layer is extracted with ethyl acetate. The combined organics are washed with water, then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue is purified on silica gel with 0 to 25% THF in hexanes to give 4-{[(2,4-dichloro-thiazol-5-yl)methyl]-isobutyl-amino}-piperidine-1-carboxylic acid t-butyl ester (303 mg, 31%): m/z=422 (M+1); 1H NMR (250 MHz, CDCl3): δ=4.35 (2H, brd), 3.87 (2H, s), 2.80 (3H, m), 2.42 (2H,d), 1.86 (3H, m), 1.61 (11H, m), 1.06 (6H, d).

후처리

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted with ethyl acetate
  3. washThe combined organics are washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified on silica gel with 0 to 25% THF in hexanes

출처 및 근거

ORD 기록
ord-ef5604f391264041b22e798313ca9b66
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07521462B2

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