2,2-Dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-(2-fluoro-5-nitro-benzyl)-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester → 2,2-Dimethyl-propionic acid 8-(4-acetylamino-benzyl)-1-(5-amino-2-fluoro-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester

HRID 720626노트

반응식

HRID 720626 반응식
[C:1]([NH:4][C:5]1[CH:45]=[CH:44][C:8]([CH2:9][C:10]2[N:18]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]3[C:16](=[O:27])[N:15]([CH2:28][C:29]4[CH:34]=[C:33]([N+:35]([O-])=O)[CH:32]=[CH:31][C:30]=4[F:38])[C:14](=[O:39])[N:13]([CH2:40][CH2:41][CH2:42][CH3:43])[C:12]=3[N:11]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([NH:4][C:5]1[CH:45]=[CH:44][C:8]([CH2:9][C:10]2[N:18]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]3[C:16](=[O:27])[N:15]([CH2:28][C:29]4[CH:34]=[C:33]([NH2:35])[CH:32]=[CH:31][C:30]=4[F:38])[C:14](=[O:39])[N:13]([CH2:40][CH2:41][CH2:42][CH3:43])[C:12]=3[N:11]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 587392302,2-Dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-(2-fluoro-5-nitro-benzyl)-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 587392272,2-Dimethyl-propionic acid 8-(4-acetylamino-benzyl)-1-(5-amino-2-fluoro-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester수율 95.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-(2-fluoro-5-nitro-benzyl)-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester (45 mg, 0.07 mmol) in methanol (30 mL) was treated with 10% palladium on carbon (45 mg). The reaction mixture was subjected to 48 psi pressure of hydrogen gas in a Parr apparatus for 2 h. At this time, the reaction mixture was filtered through a pad of celite and washed with methanol. The filtrate was concentrated in vacuo to afford 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-1-(5-amino-2-fluoro-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester (39.8 mg, 92.9%) as an off-white solid: LR-MS for C31H37FN6O5 (M−H)+ at m/z=591.

후처리

  1. filtrationAt this time, the reaction mixture was filtered through a pad of celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-f3367e6eb936465c8a1e93263840df17
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135475B2

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