Triphenylphosphine → HCID 69362088, compound

HRID 1167169Notes

Reaction equation

HRID 1167169 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([OH:40])=[C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:30]=3)[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[F:20].O[C@H:42]1[CH2:46][CH2:45][O:44][CH2:43]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:40][C@@H:42]4[CH2:46][CH2:45][O:44][CH2:43]4)=[C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:30]=3)[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[F:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 135767195295330-62-0

Product 1

HCID 69362088HCID 69362088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.03 ml Diethyl azodicarboxylate are added dropwise to a solution of 8.00 g 4-[(3-chloro-4-fluoro-phenyl)amino]-6-benzyloxy-7-hydroxy-quinazoline (see WO 0055141 A1) and 2.42 ml (S)-(+)-3-hydroxy-tetrahydrofuran and 7.95 g triphenylphosphine in 160 ml tetrahydrofuran. The reaction mixture is stirred overnight at room temperature and subsequently concentrated by evaporation in the rotary evaporator. The flask residue is purified chromatographically on a silica gel column with methylene chloride/ethyl acetate (gradient from 2:1 to 1:2) as eluant.

Workup

  1. concentrationsubsequently concentrated by evaporation in the rotary evaporator
  2. customThe flask residue is purified chromatographically on a silica gel column with methylene chloride/ethyl acetate (gradient from 2:1 to 1:2) as eluant

Sources & evidence

ORD record
ord-3c0024d0461146f291fc6c9790fc5e68
Source dataset
uspto-grants-2003_09
Patent number
US06617329B2

Reaction notes

Loading…