Sodium hydride → HCID 11212242, 화합물

HRID 349357

반응식

HRID 349357 반응식
[H-].[Na+].COP([CH2:9][C:10](=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)(=O)OC.[CH3:20][O:21][C:22](=[O:38])[CH2:23][O:24][CH2:25][C:26]#[C:27][CH2:28][N:29]1[C:34](=[O:35])[CH2:33][CH2:32][CH2:31][C@@H:30]1[CH:36]=O>C1COCC1>[CH3:20][O:21][C:22](=[O:38])[CH2:23][O:24][CH2:25][C:26]#[C:27][CH2:28][N:29]1[C:34](=[O:35])[CH2:33][CH2:32][CH2:31][C@@H:30]1/[CH:36]=[CH:9]/[C:10](=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 12989750Dimethyl [3-(3-chlorophenyl)-2-oxopropyl]phosphonateHCID 86595300HCID 86595300, 화합물

생성물 1

HCID 11212242HCID 11212242, 화합물수율 68.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Sodium hydride (60% dispersion in oil, 15 mg, 0.39 mmol) was added to a solution of [3-(3-chlorophenyl)-2-oxopropyl]-phosphonic acid dimethyl ester (97 mg, 0.35 mmol) in THF (1.5 mL) at 0° C. After 1 h at 0° C., a solution of [4-((R)-2-formyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetic acid methyl ester (0.37 mmol, crude) in THF (1.5 mL) was added via cannula. The reaction was allowed to warm to rt. After 18 h at rt, the reaction was quenched with aqueous acetic acid (50%, 15 mL) and extracted with EtOAc (3×15 mL). The combined organic phase was washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (20% →30% EtOAc/CH2Cl2, gradient) afforded 100 mg (68%) of the title compound.

후처리

  1. waitAfter 18 h at rt
  2. customthe reaction was quenched with aqueous acetic acid (50%, 15 mL)
  3. extractionextracted with EtOAc (3×15 mL)
  4. washThe combined organic phase was washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography on silica gel (20% →30% EtOAc/CH2Cl2, gradient)

출처 및 근거

ORD 기록
ord-5ae0d8fd4f2d47989293239b2f7200e8
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179820B2

연결된 노트

불러오는 중…