Triphenylphosphine → HCID 70167850、化合物

HRID 1698931ノート

反応式

HRID 1698931 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.O[CH2:26][CH2:27][CH2:28][O:29][N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:40]=[C:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38](=[O:39])[N:30]1[O:29][CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl esterHCID 222859102-(3-Hydroxy-propoxy)-isoindole-1,3-dione

生成物 1

HCID 70167850HCID 70167850、化合物収率 55.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 100 mg (0.30 mmol) of methyl (2S)-3-(4-hydroxyphenyl)-2-[(phenylmethoxy)carbonylamino]propanoate, as prepared in the preceding step, 67 mg (0.30 mmol) of 2-(3-hydroxypropoxy)isoindoline-1,3-dione, as prepared in step 2, and 88 mg (0.34 mmol) of triphenylphosphine in 10 mL THF at water/ice mixture temperature was added 66 mL (0.34 mmol) of DIAD dropwise. The solution was stirred at the same temperature for additional 20 min. Then the solution was allowed to warm to room temperature and stirred overnight. The solvent was removed under reduced pressure. The mixture was chromatographed on a silica gel column using EtOAc/hexanes (3:7 to 2:3 v/v) as eluent to yield 89 mg (55%) of viscous liquid as product: 1H NMR (300 MH, CDCl3) δ7.85-7.80 (m, 2H), 7.77-7.71 (m, 2H), 7.38-7.27 (m, 5H), 6.98 (d, J=8.65 Hz, 2H), 6.82 (d, J=8.65 Hz, 2H), 5.19 (d, J=8.16 Hz, 1H), 5.09 (s, 2H), 4.61 (m, 1H), 4.40 (t,J=6.22, 2H), 4.19 (t, J=6.11 Hz, 2H), 3.71 (s, 3H), 3.08-2.96 (m, 2H), 2.23 (quintet, J=6.15 Hz, 2H).

後処理

  1. stirringstirred overnight
  2. customThe solvent was removed under reduced pressure
  3. customThe mixture was chromatographed on a silica gel column

出典と根拠

ORDレコード
ord-9617c068beb545ed98d80a243c4eeabb
出典データセット
uspto-grants-2002_02
特許番号
US06344484B1

反応ノート

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