Tributylphosphine → Methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]-indolyl}propanoate

HRID 23985

反応式

HRID 23985 の反応式
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[OH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:23]2.[CH2:35]([O:42][C:43]([NH:45][CH2:46][CH2:47][CH2:48]O)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:35]([O:42][C:43]([NH:45][CH2:46][CH2:47][CH2:48][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:23]2)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 562256Benzyl N-(3-hydroxypropyl)carbamateHCID 22570384methyl 3-(5-hydroxy-1H-indol-2-yl)propanoate

生成物 1

HCID 22570338Methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]-indolyl}propanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1,1′-(Azodicarbonyl)dipiperidine (370 mg, 1.5 mmol) was added to the solution of methyl 3-(5-hydroxyindolyl)propanoate (220 mg, 1.0 mmol), as prepared in step g of Example 5, 3-(benzyloxycarbonylamino)propanol (230 mg, 1.1 mmol) and tri-n-butylphosphine (305 mg, 1.5 mmol) in tetrahydrofuran (20 mL). After stirring at ambient temperature overnight, the reaction mixture was concentrated and the residue was purified by flash column chromatography on silica gel (0-2% ethyl acetate in methylene chloride) to give the title compound as an off white solid (310 mg, 76%). 1H-NMR (400 MHz, CDCl3) δ 7.35 (m, 5H), 7.22 (d, J=8.9 Hz, 1H), 7.09 (d, J=3.1 Hz, 1H), 7.07 (d, J=2.1 Hz, 1H), 6.86 (dd, J=8.8, 2.4 Hz, 1H), 6.38 (d, J=2.9 Hz, 1H), 5.11 (br s, 3H), 4.41 (t, J=6.8 Hz, 2H), 4.07 (t, J=5.9 Hz, 2H), 3.66 (s, 3H), 3.44 (q, J=6.3 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 2.02 (m, 2H).

後処理

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (0-2% ethyl acetate in methylene chloride)

出典と根拠

ORDレコード
ord-b7e30da35c9f479082ec3a09dcec3b98
出典データセット
uspto-grants-2005_02
特許番号
US06855722B2

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