Acetic Acid → HCID 66932473, 화합물

HRID 518236노트

반응식

HRID 518236 반응식
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][N:14]([C:17](OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28].CC(O)=O.[C:34]1([C:40]2[S:41][CH:42]=[C:43](C=O)[N:44]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:12][CH2:13][N:14]([CH2:17][C:43]3[N:44]=[C:40]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[S:41][CH:42]=3)[CH2:15][CH2:16]1)[CH2:10][C:9]2=[O:28]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7365242-Phenyl-1,3-thiazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2회

생성물 1

HCID 66932473HCID 66932473, 화합물수율 71.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A suspension of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester hydrochloride (600 mg, 1.78 mmol, Intermediate 1) in DCM (30 ml) was treated with TEA (0.25 ml, 1.77 mmol). The pH was adjusted to 5 with AcOH and then 2-phenylthiazole-4-carbaldehyde (404 mg, 2.13 mmol) and NaBH(OAc)3 (554 mg, 2.62 mmol) were added. The mixture was stirred for 2 h at RT and then partitioned between DCM and aqueous NaHCO3 solution. The organic layer was dried over Na2SO4 and evaporated. The crude residue was purified by column chromatography (eluent: DCM/MeOH 99:1) to give (E)-3-{1′-(2-phenyl-thiazol-4-yl-methyl)-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (602 mg).

후처리

  1. custompartitioned between DCM and aqueous NaHCO3 solution
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated
  4. customThe crude residue was purified by column chromatography (eluent: DCM/MeOH 99:1)

출처 및 근거

ORD 기록
ord-98579d67f4174c918e22910e53a1dbe5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115148B2

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