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

HRID 1004215노트

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HRID 1004215 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of sodium carbonate (110.5 g) in water (1.5 liters) and L-Valyl-L-Proline tert-butyl ester in tetrahydrofuran (THF; 1 liter) 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, DMSO/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 (M+1).

후처리

  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

출처 및 근거

ORD 기록
ord-a4ce132b0f784b60a1a0a71f6658bc04
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048889

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