Methanol → (R)-methyl 2-hydroxydecanoate

HRID 1440509ノート

反応式

HRID 1440509 の反応式
[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]

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium Hydroxide2 回HCID 549544Methyl 2-hydroxydecanoate

生成物 1

HCID 10465463(R)-methyl 2-hydroxydecanoate収率 50%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-03ca8e2711fd4bd4b3ae9dddbd96b9f1
出典データセット
uspto-grants-1996_03
特許番号
US05498786

反応ノート

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