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

HRID 929948노트

반응식

HRID 929948 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d46092d8900040478233975f2f9c35bc
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296733B2

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