Sodium Bicarbonate → Methyl 3-{2-[(acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-3-methylphenyl}-2-{[(benzyloxy)carbonyl]amino}prop-2-enoate

HRID 132289

반응식

HRID 132289 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([CH3:21])=[C:11]([C:17](I)=[CH:18][CH:19]=1)[CH2:12][O:13][C:14](=[O:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]([C:26]([NH:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[CH2:27])=[O:25].C(=O)(O)[O-].[Na+]>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:22][O:23][C:24](=[O:25])[C:26]([NH:28][C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30])=[CH:27][C:17]1[CH:18]=[CH:19][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([CH3:21])[C:11]=1[CH2:12][O:13][C:14](=[O:16])[CH3:15]

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 3525700Z-Dehydro-Ala-OMeHCID 534147073-(Tert-butoxycarbonylamino)-6-iodo-2-methylbenzyl acetate

생성물 1

HCID 53415138Methyl 3-{2-[(acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-3-methylphenyl}-2-{[(benzyloxy)carbonyl]amino}prop-2-enoate수율 69%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 16212273Tetrabutylammonium chloride hydrate촉매HCID 8028Tetrahydrofuran용매

실험 절차

Palladium (II) acetate (105 mg, 0.43 mmol) was added to a mixture of acetic acid 3-tert-butoxycarbonylamino-6-iodo-2-methyl-benzyl ester (2.89 g, 7.1 mmol), Z-dehydroalanine methyl ester (2.20 g, 9.4 mmol), tetrabutylammonium chloride hydrate (2.70 g, 9.7 mmol), and sodium bicarbonate (1.80 g, 21.4 mmol) in THF (100 mL). Reaction was heated at reflux for 3.75 hours. Mixture was cooled to room temperature then filtered through a plug of silica gel eluting 70% ethyl acetate-hexanes (500 mL). Filtrate was concentrated in vacuo. Silica gel chromatography afforded the title compound as a yellow solid in 69% yield. 1H NMR (300 MHz, CDCl3): δ=7.79 (d, J=8.4, 1H), 7.42 (s, 1H), 7.27 (m, 6H), 6.30 (s, 1H), 5.11 (s, 2H), 5.02 (s, 2H), 3.81 (s, 3H), 2.21 (s, 3H), 2.02 (s, 3H), 1.51 (s, 9H). MS m/e (M−H)−=511.0.

후처리

  1. customReaction
  2. temperaturewas heated
  3. temperatureat reflux for 3.75 hours
  4. filtrationthen filtered through a plug of silica gel eluting 70% ethyl acetate-hexanes (500 mL)
  5. concentrationFiltrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-439f2396daaf45e8a85daf34b08fefa2
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

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