Sodium borohydride → Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate

HRID 371336노트

반응식

HRID 371336 반응식
[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[BH4-].[Na+]>C(O)C>[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH:12]([OH:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 20273770Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-oxoheptanoate

생성물 1

HCID 20273773Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate수율 67.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 16 (about 4 mg) in ethanol (0.5 mL) at 0° was added sodium borohydride (3 mg). The mixture was stirred at 0° for one hour and then quenched with one drop of acetic acid. After removing ethanol, the residue was diluted with methylene chloride and washed with saturated sodium chloride. The separated aqueous layer was extracted with methylene chloride twice and the combined organic layer was dried over magnesium sulfate. Removal of the solvent gave 2.7 mg of methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate, 17. By comparison of TLC mobility, this product was determined to be identical in element content to that of Example 4.

후처리

  1. customquenched with one drop of acetic acid
  2. customAfter removing ethanol
  3. additionthe residue was diluted with methylene chloride
  4. washwashed with saturated sodium chloride
  5. extractionThe separated aqueous layer was extracted with methylene chloride twice
  6. dry with materialthe combined organic layer was dried over magnesium sulfate
  7. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-d7dfa36269804f8f96af0a140e4ae333
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04530933

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