Hydrochloric Acid → tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate

HRID 1174170노트

반응식

HRID 1174170 반응식
[CH2:1]([C@H:8]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:9][C@H:10]([OH:40])[C@@H:11]([N:25](CC1C=CC=CC=1)CC1C=CC=CC=1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.C(OCC)(=O)C.O1CCOCC1.[OH-].[OH-].[Pd+2]>[NH2:25][C@@H:11]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[C@@H:10]([OH:40])[CH2:9][C@@H:8]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 2

HCID 313Hydrochloric AcidHCID 42626107tert-butyl (1S,3S,4S)-1-benzyl-4-(dibenzylamino)-3-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate

생성물 1

HCID 86726181tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate

시약·촉매·용매 4

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

Method 2 A solution containing the product from Example 23P (2.7 g, 4.21 mmol) in a mixture of methanol (20 mL) and ethyl acetate (20 mL) was treated with 20% Pd(OH)2 on carbon (1 g) and an HCl solution in dioxane (2 mL, 4 N), stirred under an atmosphere of hydrogen (balloon pressure) for 16 hours at 25° C., heated to 60° C. for 6 hours. The reaction cooled and filtered through celite®, and concentrated. The residue was partitioned between dichloromethane and half-saturated NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated to give the title compound, which was used without further purification.

후처리

  1. temperatureThe reaction cooled
  2. filtrationfiltered through celite®
  3. concentrationconcentrated
  4. customThe residue was partitioned between dichloromethane and half-saturated NaHCO3
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4e33ce35fbf84a108f0a70385b2c0ff3
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834043B2

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