Citric Acid → HCID 53987300, 화합물

HRID 977528노트

반응식

HRID 977528 반응식
[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:2]([C:7](OC)=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.C(O)C>[C:14]([O:13][C:11]([NH:1][C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:7][OH:8])=[O:12])([CH3:17])([CH3:16])[CH3:15]

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 75487913(R)-Methyl 2-((tert-butoxycarbonyl)amino)hexanoate

생성물 1

HCID 53987300HCID 53987300, 화합물수율 0.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Boc-DNle-OMe (4.23 g) in dry THF (30 ml) were added lithium chloride (0.85 g), sodium borohydride (0.76 g) and dry ethanol (60 ml), and the mixture was stirred at the same temperature for 2 h and at room temperature over night. The mixture was cooled with ice-water, adjusted to pH 3 by the gradual addition of 10% aq. citric acid, and concentrated in vacuo. Water (200 ml) was added to the residue, and the mixture was extracted with dichloromethane (50 ml×3). The combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=1/1 for elution to give the product (2.95 mg).

후처리

  1. concentrationconcentrated in vacuo
  2. additionWater (200 ml) was added to the residue
  3. extractionthe mixture was extracted with dichloromethane (50 ml×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=1/1 for elution

출처 및 근거

ORD 기록
ord-5fcf2839cc364d20baf6ca2c047b74d2
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614498

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