Hydrochloric Acid → (4R)-1-{[(3,5-dichlorophenyl)amino]carbonyl}-4-hydroxy-L-proline

HRID 1268760ノート

反応式

HRID 1268760 の反応式
[CH2:1]1[C@@H:5]([C:6]([OH:8])=[O:7])[NH:4][CH2:3][C@@H:2]1[OH:9].C([O-])([O-])=O.[K+].[K+].[Cl:16][C:17]1[CH:18]=[C:19]([N:24]=[C:25]=[O:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1.Cl>O.C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25]([N:4]2[CH2:3][C@H:2]([OH:9])[CH2:1][C@H:5]2[C:6]([OH:8])=[O:7])=[O:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 5810L-HydroxyprolineHCID 11430Potassium CarbonateHCID 944603,5-Dichlorophenyl isocyanate

生成物 1

HCID 60073589(4R)-1-{[(3,5-dichlorophenyl)amino]carbonyl}-4-hydroxy-L-proline収率 78.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a clear solution of L-trans-4-hydroxy-proline (10 g) (0.076 mol) and K2CO3 (15.7 g) (1.1 eq.) in 100 mL of water and 10 mL of THF, was added by portions 3,5-dichlorophenyl isocyanate (15.7 g) (1.1 eq.). The white suspension was stirred at RT overnight. The aqueous mixture was acidified with conc. HCl, ,then extracted with EtOAc. The organic extracts were combined, washed with water, dried over MgSO4, filtered, and the solvent removed in vacuo to afford the titled compound (19 g) (yield 78.5%). 1H NMR (DMSOd6): 8.7 (1H,COOH), 7.65 (2H,d), 7.1 (1H,m), 5.2 (1H,NH), 4.4 (2H,m), 3.6 (1H,dd), 3.45 (1H,d), 2.1–2.25 (1H, m), 1.85–2.05 (1H,m).

後処理

  1. extractionextracted with EtOAc
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-3150bd79e7954965aebf4000c636840d
出典データセット
uspto-grants-2007_04
特許番号
US07199125B2

反応ノート

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