Sodium Hydroxide → (2S,3R)-2-amino-3-hydroxy-N-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-yl}butyramide

HRID 1401782노트

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HRID 1401782 반응식
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[N:15]=[C:16]([N:19]4[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]4)[S:17][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC.C(OC([NH:66][C@H:67]([C:71](O)=[O:72])[C@@H:68]([CH3:70])[OH:69])=O)(C)(C)C.[OH-].[Na+]>C1COCC1.CC(=O)OCC>[NH2:66][C@@H:67]([C@H:68]([OH:69])[CH3:70])[C:71]([NH:25][CH:22]1[CH2:23][CH2:24][N:19]([C:16]2[S:17][CH:18]=[C:14]([C:6]3[CH:5]=[CH:4][C:3]4[C:2]([CH3:26])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=4[CH:7]=3)[N:15]=2)[CH2:20][CH2:21]1)=[O:72]

참가 물질

9

반응물 6

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724766N-tert-Butoxycarbonyl-L-threonineHCID 27960291-Hydroxybenzotriazole hydrateHCID 53312200HCID 53312200, 화합물

생성물 1

HCID 67323746(2S,3R)-2-amino-3-hydroxy-N-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-yl}butyramide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

190 mg (0.47 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine were dissolved in 5 ml of THF, and 86 mg (0.56 mmol) of 1-hydroxybenzotriazole hydrate, 239 μl (1.40 mmol) of N-ethyldiisopropylamine, 108 mg (0.56 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 113 mg (0.56 mmol) of N-(tert-butoxycarbonyl)-L-threonine were added. The mixture was stirred at room temperature overnight, dissolved in EA and 1 N NaOH and shaken. The organic phase was washed with water, dried over sodium sulfate, filtered and evaporated. The protecting group was cleaved off as already described using HCl in dioxane. The product was purified by means of preparative HPLC and is in the form of the hydrochloride.

후처리

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified by means of preparative HPLC

출처 및 근거

ORD 기록
ord-83e3c50a5dbe4f60a639f896333d3818
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907098B2

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