Hydrochloric Acid → HCID 66661172, 화합물

HRID 1913318

반응식

HRID 1913318 반응식
[F:1][C:2]([F:13])([CH3:12])[CH2:3][C@H:4]([N:9]=[C:10]=[O:11])[C:5]([O:7]C)=[O:6].C(=O)([O-])O.[Na+].[CH2:19]1[C:24]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][NH:21][CH2:20]1.[Li+].[OH-].Cl>C1COCC1.C(OCC)(=O)C>[CH2:19]1[C:24]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][N:21]([C:10]([NH:9][C@@H:4]([CH2:3][C:2]([F:13])([F:1])[CH3:12])[C:5]([OH:7])=[O:6])=[O:11])[CH2:20]1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 4174123-Azaspiro(5.5)undecane hydrochlorideHCID 516892Sodium BicarbonateHCID 57946243HCID 57946243, 화합물

생성물 1

HCID 66661172HCID 66661172, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

252 mg (1.3 mmol) of the isocyanate from example 7 were dissolved at 0° C. in 5 ml of THF and admixed with 109 mg (3.25 mmol, 2.5 eq.) of sodium hydrogencarbonate and 209 mg (1.37 mmol, 1.05 eq.) of 3-azaspiro[5.5]undecane. The mixture was stirred overnight, precipitated salts were removed and the reaction mixture was treated directly with 2.5 ml of 1 M LiOH solution (2.5 mmol, 1.9 eq.). The reaction was monitored by HPLC-MS. When the mass peak of the reactant had disappeared completely, the mixture was acidified cautiously with dilute HCl and the product was isolated by extraction with ethyl acetate, drying of the organic phase over sodium sulfate and concentration under reduced pressure. Yield: 440 mg (quantitative). The crude product was used directly in the amide coupling which follows.

후처리

  1. customprecipitated salts
  2. customwere removed
  3. dry with materialdrying of the organic phase over sodium sulfate and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-913ce297e0d74b2692a1d17977f7b5e1
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609681B2

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