Tetrahydrofuran → HCID 86727234, 화합물

HRID 716024노트

반응식

HRID 716024 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@@H:17]([O:19][CH3:20])[CH3:18])[C:13](OC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@@H:12]([C@@H:17]([O:19][CH3:20])[CH3:18])[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 69348486HCID 69348486, 화합물

생성물 1

HCID 86727234HCID 86727234, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-methoxybutanoate (prepared according to the literature procedure: Bioorg. Med. Chem. Lett. 15 (2005) 1447-1449, 1.60 g, 5.68 mmol) in a 3:1 mixture of tetrahydrofuran and methanol (12 mL), sodium borohydride (0.43 g, 11.38 mmol) was added and the mixture was stirred at room temperature for 2 hours. The volatiles were removed and the residue was dissolved in ethyl acetate (25 mL) and washed with brine (10 mL). Removal of the solvent afforded crude product which was purified by silica gel column chromatography using a gradient of ethyl acetate in pet. ether. Yield: 1.32 g (92%). 1H NMR (400 MHz, DMSO-d6) δ: 1.01 (d, 3H), 3.22 (s, 3H), 3.36-3.42 (m, 3H), 3.57-3.60 (m, 1H), 4.57 (t, 1H), 5.02 (s, 2H), 6.98-7.01 (m, 1H), 7.31-7.37 (m, 5H). MS (ES) MH+: 254.4 for C13H19F3NO4.

후처리

  1. additionwas added
  2. customThe volatiles were removed
  3. dissolutionthe residue was dissolved in ethyl acetate (25 mL)
  4. washwashed with brine (10 mL)
  5. customRemoval of the solvent
  6. customafforded crude product which
  7. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bc9bffbcf6594ab6b23bc1b084ede7a9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187495B2

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