Sodium Hydroxide → Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid

HRID 1058443ノート

反応式

HRID 1058443 の反応式
[OH-].[Na+].C[O:4][C:5](=[O:39])/[C:6](/[NH:18][C:19](=[O:38])[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([OH:36])[CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[CH:22][C:21]=1[Cl:37])=[CH:7]/[C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2>CO.O1CCCC1>[Cl:37][C:21]1[CH:22]=[C:23]([CH:26]([OH:36])[CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)[CH:24]=[CH:25][C:20]=1[C:19]([NH:18]/[C:6](=[CH:7]\[C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)/[C:5]([OH:39])=[O:4])=[O:38]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 59038366Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester

生成物 1

HCID 59038465Rac.-(z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid収率 66%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

An aqueous solution of sodium hydroxide (1N; 0.5 mL, 0.5 mmol) was added to a solution of rac.-(Z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester (Example 228; 82 mg, 0.16 mmol) in methanol/tetrahydrofuran (1:1; 2 mL). The solution was stirred at room temperature for 16 h and the solvent was evaporated. Water (3 mL) was added and the mixture was acidified with 1N hydrochloric acid solution (0.25 mL). The precipitated solids were recovered by filtration, washed with water, dried and crystallized from tetrahydrofuran/methanol/water to give rac.-(Z)-2-[[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid (53 mg, 66% yield) as a colorless solid.

後処理

  1. customthe solvent was evaporated
  2. additionWater (3 mL) was added
  3. filtrationThe precipitated solids were recovered by filtration
  4. washwashed with water
  5. customdried
  6. customcrystallized from tetrahydrofuran/methanol/water

出典と根拠

ORDレコード
ord-27424588d9114980a3f79f70f9741096
出典データセット
uspto-grants-2003_02
特許番号
US06515124B2

反応ノート

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