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tert-Butylsulfinamide, (R)-(+)- → tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]-N-[(3Z)-3-tert-butylsulfanylimino-3-phenylpropyl]carbamate

HRID 1523256
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HRID 1523256 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][C:20](=O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[CH3:28][C:29]([S@:32]([NH2:34])=O)([CH3:31])[CH3:30]>C1COCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19]/[C:20](=[N:34]/[S:32][C:29]([CH3:31])([CH3:30])[CH3:28])/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1
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반응물 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 58237945(S)-tert-butyl 1-(4-bromophenyl)ethyl(3-oxo-3-phenylpropyl)carbamate

생성물 1

HCID 87552777tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]-N-[(3Z)-3-tert-butylsulfanylimino-3-phenylpropyl]carbamate수율 55.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360
Sodium chloride; water
용매

실험 절차

A mixture of (S)-tert-butyl 1-(4-bromophenyl)ethyl(3-oxo-3-phenylpropyl)carbamate (30 g, 0.069 mol), (R)-2-methylpropane-2-sulfinamide (8.42 g, 0.069 mol), and Ti(i-OPr)4 (31.4 g, 0.138 mol) in THF (300 mL) was heated to reflux overnight. The mixture was treated with brine, and the precipitate was filtered. The filtrate was concentrated to give (S,Z)-tert-butyl 1-(4-bromophenyl)ethyl(3-(tert-butylthioimino)-3-phenylpropyl)carbamate (20 g, 55%) which was used in the next step without further purification. 1H NMR (CDCl3): δ=1.23 (s, 9H), 1.32 (s, 9H), 1.46 (d, 3H), 1.70-1.86 (m, 2H), 3.24-3.75 (m, 2H), 4.08 (m, 1H), 7.09-7.91 (m, 9H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationthe precipitate was filtered
  4. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-5e0fcb4797ea4b7db7d93774356a4a1e
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079861B2

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