Sodium Hydroxide → HCID 58778919、化合物

HRID 1372612ノート

反応式

HRID 1372612 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][O:27][CH:28]3[CH2:33][CH2:32][CH:31]([C:34]([O:36]C)=[O:35])[CH2:30][CH2:29]3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][O:27][CH:28]3[CH2:29][CH2:30][CH:31]([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 58778867HCID 58778867、化合物

生成物 1

HCID 58778919HCID 58778919、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

In THF (10 ml) and methanol (5 ml) was dissolved methyl 4-(1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylate (580 mg, 1.1 mmol), that is, a mixture of two diastereomers (cis and trans forms). After addition of 1N NaOH (1.5 ml, 1.5 mmol), the mixture was stirred at 70° C. for 24 hours. The residue obtained by distilling off the solvent under reduced pressure, was acidified weakly with 1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure. The resulting crystals were washed with water and dried under reduced pressure, whereby 4-(1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylic acid was obtained as a mixture of two diasteromers. The mixture was separated by HPLC (C18 column, eluting with 0.02N acetate buffer-acetonitrile (1:1, v/v)), whereby Isomer A (150 mg, 27%) was obtained as a white crystalline solid.

後処理

  1. additiona mixture of two diastereomers (cis and trans forms)
  2. customThe residue obtained
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washThe resulting crystals were washed with water
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-72dc8c6047034c94811b32296ab65cfb
出典データセット
uspto-grants-2007_01
特許番号
US07157487B2

反応ノート

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