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

HRID 23985

Reaction equation

HRID 23985 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b7e30da35c9f479082ec3a09dcec3b98
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Linked notes

Loading…