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

HRID 2207101ノート

反応式

HRID 2207101 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2c560ca84cc74c169294a1b76d23bd3c
出典データセット
uspto-grants-2016_06
特許番号
US09376398B2

反応ノート

読み込み中…