Cesium carbonate → (S)-2-Phthalimido-6-hydroxyhexanoic acid, phenylmethyl ester

HRID 543208

反応式

HRID 543208 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+]>CO.O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:10]1[C:11](=[O:20])[C:12]2=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]2[C:14]1=[O:15])[C:7]([O:9][CH2:11][C:12]1[CH:13]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:8]

参加物

5

反応物 2

HCID 10796Cesium carbonateHCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acid

生成物 1

HCID 13851095(S)-2-Phthalimido-6-hydroxyhexanoic acid, phenylmethyl ester収率 198.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

6-Hydroxy-2(S)-phthalimidohexanoic acid (5.0 g) was dissolved in a mixture of 90 ml of methanol and 9 ml of water. To this solution, an aqueous 0.5M cesium carbonate solution (18 ml) was added and the mixture stirred for a few minutes. Most of the methanol was removed in vacuo and the resulting aqueous residue was freeze-dried. The lyophilized material was dissolved in DMF (70 ml) and treated with 3.08 g of benzyl bromide. After stirring under nitrogen for 6 hours, the reaction mixture was diluted with 450 ml of water and repeatedly extracted with ethyl acetate. Organic layers were then back-washed with water, dried (Na2SO4), and concentrated to give 6.58 g of benzyl 6-hydroxy-2(S)-phthalimidohexanoate. Recrystallization from ether gave a white solid, m.p. 106.5°-108°; [α]D25° =-27.6° (MeOH, c=1.77).

後処理

  1. customMost of the methanol was removed in vacuo
  2. customthe resulting aqueous residue was freeze-dried
  3. dissolutionThe lyophilized material was dissolved in DMF (70 ml)
  4. additiontreated with 3.08 g of benzyl bromide
  5. stirringAfter stirring under nitrogen for 6 hours
  6. additionthe reaction mixture was diluted with 450 ml of water
  7. extractionrepeatedly extracted with ethyl acetate
  8. washOrganic layers were then back-washed with water
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-2059ff4320184caa89158e76fd251f53
出典データセット
uspto-grants-1987_04
特許番号
US04661479

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