Acetic Acid → tert-butyl(2S,3S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3-methylpentanoate

HRID 216278

반응식

HRID 216278 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]=O.Cl.[C:16]([O:20][C:21](=[O:28])[C@H:22]([C@H:24]([CH2:26][CH3:27])[CH3:25])[NH2:23])([CH3:19])([CH3:18])[CH3:17].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][NH:23][C@@H:22]([C@@H:24]([CH3:25])[CH2:26][CH3:27])[C:21]([O:20][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:28]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 76201Phthalylglycine aldehydeHCID 5003444Sodium cyanoborohydrideHCID 11687228tert-Butyl isoleucinate--hydrogen chloride (1/1)

생성물 1

HCID 66891692tert-butyl(2S,3S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3-methylpentanoate수율 61.7%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
25 °C

실험 절차

To a solution of Example 32A (12.1 g) in methanol (20 mL) was added L-isoleucine tert-butyl ester hydrochloride (13.0 g, 58 mmol), sodium cyanoborohydride (7.3 g, 116 mmol), and acetic acid (2 mL). The resulting solution was stirred for 3 hrs at 25° C. and the methanol removed under vacuum, dichloromethane (500 mL) added, and the solution extracted with aq. NaHCO3 (2×300 mL). Evaporation and purification of the organic layer gave 12.9 g of the title compound.

후처리

  1. customthe methanol removed under vacuum, dichloromethane (500 mL)
  2. additionadded
  3. extractionthe solution extracted with aq. NaHCO3 (2×300 mL)
  4. customEvaporation and purification of the organic layer

출처 및 근거

ORD 기록
ord-f290d33003ad48f9a248d0591c3166ef
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193227B2

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