Methyl chloroformate → N-(methoxycarbonyl)-L-valyl-L-proline tert-butyl ester

HRID 2293802ノート

反応式

HRID 2293802 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]([O:10][CH3:11])=[O:9].[C:12]([O:16][C:17](=[O:30])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23](=[O:29])[C@H:24]([CH:26]([CH3:28])[CH3:27])[NH2:25])([CH3:15])([CH3:14])[CH3:13]>O.O1CCCC1.CCOCC>[C:12]([O:16][C:17](=[O:30])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23](=[O:29])[C@H:24]([CH:26]([CH3:27])[CH3:28])[NH:25][C:8]([O:10][CH3:11])=[O:9])([CH3:14])([CH3:13])[CH3:15]

参加物

7

反応物 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 11196516tert-butyl (2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylate

生成物 1

HCID 54370033N-(methoxycarbonyl)-L-valyl-L-proline tert-butyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of sodium carbonate (110.5 g) in water (1.5 litres) and L-Valyl-L-Proline tert-butyl ester in tetrahydrofuran (THF; 1 litre) were combined and cooled to 0° C. The mixture was diluted with ether (400 ml) and methyl chloroformate (39.4 g) was added dropwise. The reaction mixture was then allowed to warm ambient temperature over 2 hours. The layers were separated and the organic phase was washed twice with 1M hydrochloric acid, followed by saturated aqueous sodium bicarbonate solution and brine. The aqueous phase was extracted with ether. All organic phases were combined and dried (MgSO4) and the solvent removed to give N-(methoxycarbonyl)-L-valyl-L-proline tert-butyl ester (125.9 g); 1H NMR (300 MHz, DHSO/d4-trifluoroacetic acid): 4.23 (dd, 1H), 4.06 (d, 1H), 3.78 (m, 1H), 3.57 (m, 1H), 3.55 (s, 3H), 2.16 (m, 1H), 1.95 (m, 3H), 1.80 (m, 1H), 1.42 (s, 9H), 0.94 (m, 6H); MS: m/z=329 (H+1).

後処理

  1. additionwas added dropwise
  2. temperatureto warm ambient temperature over 2 hours
  3. customThe layers were separated
  4. washthe organic phase was washed twice with 1M hydrochloric acid
  5. extractionThe aqueous phase was extracted with ether
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed

出典と根拠

ORDレコード
ord-2e2db1cacdb143a6ae6bfb2ac4cfb6ad
出典データセット
uspto-grants-1997_11
特許番号
US05686628

反応ノート

読み込み中…