Methanol → (R)-1-(4-((2-amino-4-((S)-1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)pyrrolidine-2-carboxylic acid

HRID 2207101노트

반응식

HRID 2207101 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])[C:5]([CH2:16][C:17]2[CH:35]=[CH:34][C:20]([CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C@@H:23]3[C:27]([O:29]C(C)(C)C)=[O:28])=[CH:19][C:18]=2[O:36][CH3:37])=[C:4]([CH3:38])[N:3]=1.FC(F)(F)C(O)=O.CO>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])[C:5]([CH2:16][C:17]2[CH:35]=[CH:34][C:20]([CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C@@H:23]3[C:27]([OH:29])=[O:28])=[CH:19][C:18]=2[O:36][CH3:37])=[C:4]([CH3:38])[N:3]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 117992865(R)-tert-butyl 1-(4-((2-amino-4-((S)-1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)pyrrolidine-2-carboxylate

생성물 1

HCID 72549259(R)-1-(4-((2-amino-4-((S)-1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)pyrrolidine-2-carboxylic acid수율 79.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of the product of step (ii) (70 mg) in chloroform (1.5 mL) was added trifluoroacetic acid (1.5 mL) and the mixture was stirred at RT. After 12 h, methanol (10 mL) was stirred at room temperature. After 12 h, the mixture was concentrated under reduced pressure. 10% aqueous potassium dicarbonate was added and the resulting mixture was extracted with chloroform/EtOH (3/1). The combined organic layer was dried and concentrated under reduced pressure to afford the sub-title compound (50 mg) as a white solid; 1H NMR (methanol-d4); 7.23 (1H, d), 7.02-6.97 (2H, m), 4.47 (1H, m), 4.34 (2H, s), 3.97 (3H, s), 3.85-3.80 (3H, m), 3.64 (1H, m), 3.45-3.41 (2H, m), 2.44 (1H, m), 2.28 (3H, s), 2.11 (2H, m), 1.96 (1H, m), 1.74-1.20 (7H, m), 0.87 (3H, t); LC-MS: m/z 472.

후처리

  1. waitAfter 12 h
  2. concentrationthe mixture was concentrated under reduced pressure
  3. addition10% aqueous potassium dicarbonate was added
  4. extractionthe resulting mixture was extracted with chloroform/EtOH (3/1)
  5. customThe combined organic layer was dried
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2c560ca84cc74c169294a1b76d23bd3c
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376398B2

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