Lithium Hydroxide → 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid

HRID 889061ノート

反応式

HRID 889061 の反応式
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[NH:26][C:25]4[C:24](=[O:27])[N:23]([CH2:28][CH2:29][CH3:30])[C:22](=[O:31])[N:21]([CH2:32][CH2:33][CH3:34])[C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:7][N:6]1[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=1)=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[O:31]=[C:22]1[N:21]([CH2:32][CH2:33][CH3:34])[C:20]2[N:19]=[C:18]([C:15]3[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH:8]4[CH2:7][N:6]([CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:44])([F:45])[F:43])[CH:37]=5)[CH:5]([C:3]([OH:4])=[O:2])[CH2:9]4)=[CH:17][CH:16]=3)[NH:26][C:25]=2[C:24](=[O:27])[N:23]1[CH2:28][CH2:29][CH3:30]

参加物

6

反応物 2

HCID 3939Lithium HydroxideHCID 579887864-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid methyl ester

生成物 1

HCID 442364494-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of solution of 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid methyl ester (25 mg, 0.039 mmol) in THF (3 ml) and MeOH (1 ml) was added aq. solution of LiOH (3 mg, 0.079 mmol) in H2O (1 ml) at 0° C. and it was stirred for 2 hrs. Reaction mixture was concentrated, residue was diluted with water and acidified with aq. HCl. The aqueous layer was extracted with ethyl acetate and washed with brine. The ethyl acetate layer was concentrated and purified by column chromatography to offer 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid as viscous oil (18 mg, 75%).

後処理

  1. customReaction mixture
  2. concentrationwas concentrated
  3. additionresidue was diluted with water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. concentrationThe ethyl acetate layer was concentrated
  7. custompurified by column chromatography

出典と根拠

ORDレコード
ord-5b874389b46e498ca0ef6ccf2351a4f3
出典データセット
uspto-grants-2012_08
特許番号
US08252797B2

反応ノート

読み込み中…