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Triphenylphosphine → tert-Butyl 3-((4-((S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenylcarbamate

HRID 2235599
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HRID 2235599 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.[CH2:17]([C@H:24]1[CH2:28][O:27][C:26](=[O:29])[N:25]1[C:30](=[O:45])[CH2:31][C@@H:32]([C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)[C:33]1[CH:37]=[CH:36][O:35][N:34]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:17]([C@H:24]1[CH2:28][O:27][C:26](=[O:29])[N:25]1[C:30](=[O:45])[CH2:31][C@@H:32]([C:38]1[CH:39]=[CH:40][C:41]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:6]=[CH:7][CH:8]=2)=[CH:42][CH:43]=1)[C:33]1[CH:37]=[CH:36][O:35][N:34]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 14523557tert-Butyl (3-(hydroxymethyl)phenyl)carbamateHCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

생성물 1

HCID 59300702tert-Butyl 3-((4-((S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenylcarbamate
수율 96.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of alcohol 27.1 (179 mg, 0.765 mmol) in THF (7 mL), was added phenol 7.5 (300 mg, 0.765 mmol), DIAD (0.155 mL, 0.803 mmol), and triphenylphosphine (211 mg, 0.803 mmol). The solution was stirred for 16 hours and then concentrated to a reduced volume. The residue was purified by medium pressure chromatography (silica gel, 0 to 50% EtOAc:hexanes) to give 27.2 (440 mg). MS ESI (pos.) m/e 598.2 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 8.20 (1H, d, J=1.6 Hz), 7.38 (1H, s), 7.08-7.29 (8H, m), 7.00 (1H, d), 6.82 (2H, d, J=8.6 Hz), 6.54 (1H, s), 6.33 (1H, br. s.), 6.05 (1H, d, J=1.6 Hz), 4.92 (2H, s), 4.85-4.90 (1H, m), 4.66 (1H, dd, J=1.6 Hz), 4.49-4.58 (1H, m), 4.01-4.04 (1H, m), 3.93 (1H, dd, J=17.6, 8.2 Hz), 3.45 (1H, dd, J=17.6, 6.7 Hz), 3.11 (1H, dd, J=13.5, 3.3 Hz), 2.68 (1H, dd, J=13.3, 9.4 Hz), 1.43 (9H, s).

후처리

  1. concentrationconcentrated to a reduced volume
  2. customThe residue was purified by medium pressure chromatography (silica gel, 0 to 50% EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-64417975e9c04c23b57f8ab8a21f3883
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714008B2

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