Water → HCID 86610002, compound

HRID 1176400Notes

Reaction equation

HRID 1176400 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[C:7]([O:14][CH2:15][CH2:16][O:17][CH:18]2[CH:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[O:42][CH3:43])=[CH:26][CH:25]=3)[CH2:22][CH2:21][N:20]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:19]2)=[N:8][C:9]([CH3:13])=[N:10][C:11]=1[Cl:12])=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:71](OC(=O)C)(=[O:73])[CH3:72]>O1CCCC1>[C:71]([NH:1][CH2:4][CH2:5][C:6]1[C:7]([O:14][CH2:15][CH2:16][O:17][CH:18]2[CH:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[O:42][CH3:43])=[CH:26][CH:25]=3)[CH2:22][CH2:21][N:20]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:19]2)=[N:8][C:9]([CH3:13])=[N:10][C:11]=1[Cl:12])(=[O:73])[CH3:72]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11776TriphenylphosphineHCID 86610003HCID 86610003, compound

Product 1

HCID 86610002HCID 86610002, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.13 g of tert-butyl 3-{2-[5-(2-azidoethyl)-6-chloro-2-methylpyrimidin-4-yloxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 25 ml of tetrahydrofuran is admixed at room temperature successively with 3.1 ml of water, 0.54 g of triphenylphosphine and 0.74 ml of acetic anhydride. The reaction mixture is stirred at room temperature over 16 hours and subsequently concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.10 (3:1 EtOAc-heptane); Rt=5.49.

Workup

  1. concentrationsubsequently concentrated by evaporation

Sources & evidence

ORD record
ord-da2f1703d1ec4c27bcf7f279ce19851e
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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