Hydrochloric Acid → (4S,5S)-4-(Hydroxymethyl)-5-(4-(2-methoxyethoxy)phenyl)oxazolidin-2-one

HRID 929948ノート

反応式

HRID 929948 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[O:16][C:15](=[O:17])[NH:14][C@H:13]2[C:18](OC)=[O:19])=[CH:8][CH:7]=1.[BH4-].[Na+].Cl>CCO>[OH:19][CH2:18][C@H:13]1[C@H:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:11][CH:10]=2)[O:16][C:15](=[O:17])[NH:14]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86718529(4R,5S)-Methyl 5-(4-(2-methoxyethoxy)phenyl)-2-oxooxazolidine-4-carboxylate

生成物 1

HCID 86718530(4S,5S)-4-(Hydroxymethyl)-5-(4-(2-methoxyethoxy)phenyl)oxazolidin-2-one収率 86.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of (4R,5S)-methyl 5-(4-(2-methoxyethoxy)phenyl)-2-oxooxazolidine-4-carboxylate (2.30 g, 7.79 mmol) in EtOH (45 mL) was added in portions at 0-5° C. sodium borohydride (648 mg, 17.1 mmol). The reaction mixture was stirred for 0.5 h at RT and then acidified with 4M aqueous HCl (10 mL) at 0-5° C. The reaction mixture was concentrated and the product was extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound as a beige foam (1.80 g, 81%). tR=0.498 min (UPLC 1); LC-MS: [M+H] 268; Rt 0.55 min; (LCMS method 2); 1H NMR (400 MHz, CDCl3): 7.31 (d, 2H), 6.96 (d, 2H), 6.45 (br s, 1H), 5.33 (d, 1H), 5.30 (br s, 1H), 3.75-4.30 (m, 7H), 3.47 (s, 3H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe product was extracted with EtOAc
  3. washCombined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d46092d8900040478233975f2f9c35bc
出典データセット
uspto-grants-2016_03
特許番号
US09296733B2

反応ノート

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