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

HRID 1268760

반응식

HRID 1268760 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3150bd79e7954965aebf4000c636840d
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199125B2

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