Lithium Hydroxide → HCID 68764235, 화합물

HRID 79518노트

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HRID 79518 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:23]([C:24]([O:26]C)=[O:25])=[CH:22][N:21]=[C:20]3[NH:28][CH:29]=[CH:30][C:19]=23)[CH2:14][CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Li+].[OH-]>O.CO.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)[C:10]([N:12]1[CH2:13][CH2:14][N:15]([C:18]2[C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=[C:20]3[NH:28][CH:29]=[CH:30][C:19]=23)[CH2:16][CH2:17]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68765221(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridine-5-carboxylate

생성물 1

HCID 68764235HCID 68764235, 화합물수율 24.4%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 6344Dichloromethane용매

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온도
65 °C

실험 절차

(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.210 g, 0.3874 mmol, see Example 2) was placed in 2:1 THF:MeOH (6 mL). 3M LiOH (aq., 1.29 mL, 3.87 mmol) was then added, and the reaction was heated to 65° C. for 2 hours. The reaction was then diluted with water and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give a crude residue. The residue was purified by column:chromatography (20:1 DCM:MeOH) to give (R)-4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.050 g, 24.4% yield).

후처리

  1. extractionextracted with DCM
  2. customThe combined organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude residue
  6. customThe residue was purified by column

출처 및 근거

ORD 기록
ord-baaec48b8f984a179007030f6570ed0c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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