Methanol → (R)-methyl 2-hydroxydecanoate

HRID 1440509노트

반응식

HRID 1440509 반응식
[OH-].[Na+].[OH:3][CH:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5]([O:7][CH3:8])=[O:6].CO>O>[CH3:8][O:7][C:5](=[O:6])[C@H:4]([OH:3])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium Hydroxide2회HCID 549544Methyl 2-hydroxydecanoate

생성물 1

HCID 10465463(R)-methyl 2-hydroxydecanoate수율 50%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Lipase P-30 (Amano from Pseudomonas fluorescens) (1 g, 5% by weight) was dissolved in 140 ml of H2O and the pH of the solution adjusted to 7.5 with a 1N solution of NaOH. Racemic methyl 2-hydroxydecanoate (20.12 g, 0.995 mol) (CP-112,994) was added to the enzyme solution and the pH controlled to maintain a range of 6-8. The reaction was stirred at room temperature for 10 hours (total of 46.5 mL of 1N NaOH added) and worked up by addition of 140 ml of methanol. The aqueous alcohol was extracted with hexane (3×200 mL). The hexane extracts were combined and dried (MgSO4). Following concentration, the desired (R)-methyl-2-hyroxydecanoate (10.08 g, 0.049 mol, 50%) was obtained: [α]D =-3.1° (c=1, MeOH). The aqueous extracts were acidified to pH 1-2 with HCl and extracted with two portions of ethyl acetate (200 mL). The combined extracts were dried (MgSO4) and concentrated to give (S)-2-hydroxydecanoic acid (8.91 g, 0.047 mol, 47%): mp 70°-72°; [α]D =-1.7° (c=1, MeOH).

후처리

  1. temperatureto maintain a range of 6-8
  2. extractionThe aqueous alcohol was extracted with hexane (3×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentration

출처 및 근거

ORD 기록
ord-03ca8e2711fd4bd4b3ae9dddbd96b9f1
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05498786

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