Trifluoroacetic acid → (S)-ethyl 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetate

HRID 2207066

반응식

HRID 2207066 반응식
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12].[NH2:16][C:17]1[N:22]=[C:21](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)[C:20]([CH2:36][C:37]2[CH:52]=[CH:51][C:40]([CH2:41][N:42]([CH2:49][CH3:50])[CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:39][C:38]=2[O:53][CH3:54])=[C:19]([CH3:55])[N:18]=1>C(#N)CC>[NH2:16][C:17]1[N:22]=[C:21]([NH:8][C@@H:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])[C:20]([CH2:36][C:37]2[CH:52]=[CH:51][C:40]([CH2:41][N:42]([CH2:49][CH3:50])[CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:39][C:38]=2[O:53][CH3:54])=[C:19]([CH3:55])[N:18]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 11062353(S)-3-aminohexan-1-olHCID 117992606Ethyl 2-((4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetate

생성물 1

HCID 117999083(S)-ethyl 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(ethyl)amino)acetate수율 78.8%

시약·촉매·용매 1

HCID 7854Propionitrile용매

반응 조건

온도
120 °C

실험 절차

Trifluoroacetic acid (0.066 mL) was added to a mixture of (S)-3-aminohexan-1-ol (300 mg) and the product from step (vii) (490 mg) in propionitrile (5 mL). The mixture was heated at 120° C. for 16 h and cooled to RT. The solvent was removed by evaporation. The residue was purified by flash column chromatography on amino silica gel to afford the sub-title compound (330 mg) as a colourless gum; 1H NMR (CDCl3); 6.94 (1H, s), 6.88 (1H, d), 6.79 (1H, d), 4.66 (1H, d), 4.58 (2H, br s), 4.13 (2H, q), 4.11-4.06 (1H, m), 3.88 (3H, s), 3.70 (2H, s), 3.66 (2H, s), 3.42 (1H, ddd), 3.28-3.20 (3H, m), 2.65 (2H, q), 2.34 (3H, s), 1.82-1.74 (1H, m), 1.45-1.33 (1H, m), 1.26-1.21 (5H, m), 1.07-1.02 (5H, m), 0.73 (3H, t).

후처리

  1. temperaturecooled to RT
  2. customThe solvent was removed by evaporation
  3. customThe residue was purified by flash column chromatography on amino silica gel

출처 및 근거

ORD 기록
ord-6076f5c99b58431e8e2112e690ccc276
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376398B2

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