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 889061노트

반응식

HRID 889061 반응식
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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5b874389b46e498ca0ef6ccf2351a4f3
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252797B2

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