Tetrahydrofuran → HCID 86727234、化合物

HRID 336338ノート

反応式

HRID 336338 の反応式
[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>[OH:14][CH2:13][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:17]([O:19][CH3:20])[CH3:18]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 69348486HCID 69348486、化合物

生成物 1

HCID 86727234HCID 86727234、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e83fb8f13b424957a02c2942b9b0a7d7
出典データセット
uspto-grants-2014_11
特許番号
US08889671B2

反応ノート

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