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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
ノート
印刷プレビュー

反応式

HRID 2233946 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6342
Acetonitrile
溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3fbff6c67c5b4748a08558ccbcba29df
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709503B2

反応ノート

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