Hydrochloric Acid → N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide

HRID 2242330노트

반응식

HRID 2242330 반응식
[C:1]([NH:4][C@@H:5]1[CH2:10][C@H:9]([N:11]([CH:13]([CH3:15])[CH3:14])[CH3:12])[CH2:8][CH2:7][C@@H:6]1[N:16]1[CH2:20][CH2:19][C@H:18]([NH:21]C(=O)OCC2C=CC=CC=2)[C:17]1=[O:32])(=[O:3])[CH3:2].Cl>CC(O)C.[Pd]>[NH2:21][C@H:18]1[CH2:19][CH2:20][N:16]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([N:11]([CH:13]([CH3:15])[CH3:14])[CH3:12])[CH2:10][C@H:5]2[NH:4][C:1](=[O:3])[CH3:2])[C:17]1=[O:32]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 44185160benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

생성물 1

HCID 44185161N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide수율 130.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 3776Isopropanol용매

실험 절차

Example 1, Alternative Preparation, Step 6: To a solution containing acetamide 10 (˜61 g) in i-PrOH (˜625 mL) was added 10% Pd/C wet catalyst (2.5 g) and the suspension was hydrogenated at 30 psig and approx. 25° C. for at least 2 h. Upon completion (HPLC), the catalyst was removed by filtration and the filtrate was concentrated to approx. 550 mL. Water (8.8 mL) was added, followed by 5.6 N hydrochloric acid in i-PrOH solution (69.5 mL). The resulting slurry was held at room temperature overnight. The product was isolated by filtration and the cake was rinsed with i-PrOH (2×100 mL) and dried in vacuo to constant weight at ˜50° C. to give N-[(1R,2S,5R)-2-((S)-3-amino-2-oxo-pyrrolidin-1-yl)-5-(isopropyl-methyl-amino)-cyclohexyl]-acetamide 11 (55.6 g, 97% yield) as its hydrochloric acid salt (73.6% free base assay, HPLC).

후처리

  1. customExample 1, Alternative Preparation, Step 6
  2. waitthe suspension was hydrogenated at 30 psig and approx. 25° C. for at least 2 h
  3. customUpon completion (HPLC), the catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated to approx. 550 mL
  5. additionWater (8.8 mL) was added
  6. customThe product was isolated by filtration
  7. washthe cake was rinsed with i-PrOH (2×100 mL)
  8. customdried in vacuo to constant weight at ˜50° C.

출처 및 근거

ORD 기록
ord-84e12e625b17401ab6c696b7f3ba13ed
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671062B2

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