Tributylphosphine → HCID 10908472, compound

HRID 2304562Notes

Reaction equation

HRID 2304562 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[N:15]=[C:14]([I:20])[C:13]([CH2:21]O)=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][C:28](=[O:41])[CH2:29][C:30]([OH:40])([C:33]1[CH:38]=[CH:37][NH:36][C:35](=[O:39])[CH:34]=1)[CH2:31][CH3:32])([CH3:26])([CH3:25])[CH3:24].C(P(CCCC)CCCC)CCC.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:23]([O:27][C:28](=[O:41])[CH2:29][C:30]([C:33]1[CH:38]=[CH:37][N:36]([CH2:21][C:13]2[C:14]([I:20])=[N:15][C:16]3[C:11]([CH:12]=2)=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:18]([F:19])[CH:17]=3)[C:35](=[O:39])[CH:34]=1)([OH:40])[CH2:31][CH3:32])([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11047852HCID 11047852, compoundHCID 11119047HCID 11119047, compound

Product 1

HCID 10908472HCID 10908472, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture, under an argon atmosphere, of 6-benzyloxy-7-fluoro-2-iodo-3-quinolylmethanol (obtained according to 1.f, 2.05 g, 5 mmol), tert-butyl3-hydroxy-3-(2-oxo-1,2-dihydro-4-pyridinyl)pentanoate (obtained according to 1.h, 1.47 g, 5.5 mmol), and tributylphosphine (1.36 ml, 5.5 mmol) in anhydrous tetrahydrofuran (20 ml) is treated dropwise with diethyl azodicarboxylate (1.3 ml, 7.5 mmol). The reaction mixture is then agitated at ambient temperature for 6 hours, then concentrated under reduced pressure. The resulting oily residue is taken up in dichloromethane (100 ml) and washed with saturated aqueous ammonium chloride then with saturated aqueous sodium chloride. The organic phase is dried over sodium sulphate then concentrated to 5 ml and acetonitrile is added in order to obtain a white precipitate which is kept at 4° C. for 16 hours. The precipitate is collected by filtration then washed with isopropyl ether in order to produce 1.8 g (55%) of a white solid, m.p. 174° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with saturated aqueous ammonium chloride
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationthen concentrated to 5 ml and acetonitrile
  5. additionis added in order
  6. customto obtain a white precipitate which
  7. waitis kept at 4° C. for 16 hours
  8. filtrationThe precipitate is collected by filtration
  9. washthen washed with isopropyl ether in order

Sources & evidence

ORD record
ord-3d68d73c422e43e29be98c59bc6e3dd7
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

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