Sodium Hydroxide → 3-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid

HRID 1033373

반응식

HRID 1033373 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:19])([CH3:18])[CH2:13][C:14]([O:16]C)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:19])([CH3:18])[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 15042554Methyl 3-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

생성물 1

HCID 145510073-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid수율 99.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 18.27 g (68.9 mmol) of methyl 3-benzyloxycarbonylamino-3-methylbutanoate (Step D) in 20 mL of methanol at room temperature was treated dropwise wit 51 mL of 2N NaOH (102 mmol, 1.5 eq). The mixture was stirred at room temperature for 16 hours then transferred to a separatory funnel and washed with hexane (3×). The aqueous layer was removed, cooled to 0° and slowly acidified to pH 2 (paper) by dropwise addition of 6N HCl. This mixture was extracted with ether (6×); combined extracts were washed with 1N HCl and brine, then dried over magnesium sulfate, filtered and solvent removed under vacuum to afford 17.26 g (68.7 mmol, 99%) of the product. 1H NMR (200 MHz,CDCl3): 1.42 (s,6 H), 2.77 (s,2 H), 5.06 (s,2 H), 5.2 (br s,1 H), 7.3 (s,5 H).

후처리

  1. customthen transferred to a separatory funnel
  2. washwashed with hexane (3×)
  3. customThe aqueous layer was removed
  4. temperaturecooled to 0°
  5. additionslowly acidified to pH 2 (paper) by dropwise addition of 6N HCl
  6. extractionThis mixture was extracted with ether (6×)
  7. washcombined extracts were washed with 1N HCl and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customsolvent removed under vacuum

출처 및 근거

ORD 기록
ord-27fb14c00a0347f59aa0a6a7d13b7a64
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310737

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