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Hydrochloric Acid → 4-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-proline

HRID 2233946
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HRID 2233946 반응식
[OH-].[Li+].[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[NH:6][C:5]=1[C:11]([NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH:20]2[CH2:24][NH:23][C@H:22]([C:25]([O:27]C)=[O:26])[CH2:21]2)[CH2:16][CH2:15]1)=[O:12].Cl>C(#N)C.O>[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[NH:6][C:5]=1[C:11]([NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH:20]2[CH2:24][NH:23][C@H:22]([C:25]([OH:27])=[O:26])[CH2:21]2)[CH2:18][CH2:19]1)=[O:12]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68579931Methyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-prolinate

생성물 1

HCID 573942614-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-proline수율 49.9%

시약·촉매·용매 2

HCID 962Water용매
HCID 6342
Acetonitrile
용매

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온도
70 °C

실험 절차

A 2 N solution of lithium hydroxide was heated to 70° C. Methyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-prolinate (Example 52, 0.081 g, 0.20 mM) in acetonitrile (1.1 ml) and water (0.4 ml) was added to the solution and stirred at 70° C. for ten minutes then ambient temperature for twenty minutes. 1 N Hydrogen chloride was added and a minor impurity was extracted using EtOAc. The aqueous layer was lyophilized to give an orange solid that was purified by HPLC eluting CH3CN/H2O (0.1% TFA). Relevant fractions were collected, concentrated and lyophilized to give the desired product as a light orange solid (0.039 g).

후처리

  1. waitambient temperature for twenty minutes
  2. extractiona minor impurity was extracted
  3. customto give an orange solid
  4. customthat was purified by HPLC
  5. washeluting CH3CN/H2O (0.1% TFA)
  6. customRelevant fractions were collected
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3fbff6c67c5b4748a08558ccbcba29df
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709503B2

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