美司坦 → Methyl 2-amino-3-(3,7,11-trimethyldodeca-2,6,10-trienylsulfanyl)propanoate

HRID 20195

反应方程式

HRID 20195 反应方程式
[CH3:1][O:2][C:3](=[O:8])[C@H:4]([CH2:6][SH:7])[NH2:5].[CH2:9](Br)[CH:10]=[C:11]([CH2:13][CH2:14][CH:15]=[C:16]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH3:17])[CH3:12]>N.CO>[CH3:1][O:2][C:3](=[O:8])[CH:4]([NH2:5])[CH2:6][S:7][CH2:9][CH:10]=[C:11]([CH3:12])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:17])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22]

参与物

4

反应物 2

HCID 29145美司坦HCID 550199反，反-法尼基溴

产物 1

HCID 1304Methyl 2-amino-3-(3,7,11-trimethyldodeca-2,6,10-trienylsulfanyl)propanoate收率 74%

试剂、催化剂与溶剂 1

HCID 21705897Ammonia methanol溶剂

反应条件

温度
0 °C

实验过程

Into a 100 mL round bottomed flask at 0° C. is added L-Cysteine methyl ester (1.38 g, 10.2 mmols) in 60 mL of 7M NH3/MeOH. Neat farnesyl bromide (1b) (1.00 g 3.52 mmols) is then added and the solution is stirred at 0° C. for four hours. The reaction mixture is partitioned between ether and water and extracted 3× with ether, extracts are combined, dried over MgSO4 filtered and evaporated. Purification by flash chromatography (1% MeOH:CHCl3) yields 881 mg (74%) of a clear oil. Rf=0.22 in 5% MeOH in CHCl3. 1H NMR (CDCl3, 400 MHz): 5.24 (t, 1H, J=8 Hz), 5.10 (m, 2H), 3.75 (s, 3H), 3.64 (q, 1H), 3.10-3.25 (m, 2H), 2.86-2.91 (2d, 1H), 2.65-2.71 (2d, 1H), 2.04-2.10 (m, 6H), 2.04(m, 6H) 2.0 (t, 2H), 1.69 (s, 3H), 1.68 (s. 3H), 1.60 (s, 6H); 13C NMR (CDCl3, 50 MHz) 174.93, 139.91, 135.71, 131.62, 124.69, 124.11, 120.35, 54.64, 52.35, 39.93, 36.77, 30.15, 26.98, 26.67, 25.86, 17.86, 16.33, 16.21 MS: (ESI, +) (M−H+) 340

后处理

  1. customThe reaction mixture is partitioned between ether and water
  2. extractionextracted 3× with ether, extracts
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (1% MeOH:CHCl3)

来源与证据

ORD记录
ord-46208ccbb88746418c0b9b19091ee589
来源数据集
uspto-grants-2010_06
专利号
US07745589B1

关联笔记

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