Trifluoroacetic acid → HCID 24902681, compound

HRID 1916256Notes

Reaction equation

HRID 1916256 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.[OH:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1>>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[O:15][CH:16]1[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 744042-ChloropyrimidineHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 24902681HCID 24902681, compound

Procedure

Compound P23 was prepared according to the general procedure described in the preparation of P21 in Preparation 21, except that 2-chloropyrimidine was employed instead of 2-bromopyridine, to afford P23. 1H NMR (400 MHz, CDCl3) δ 1.42 (s, 9H), 4.02 (m, 2H), 4.30 (m, 2H), 5.29 (m, 1H), 6.97 (t, J=4.9 Hz, 1H), 8.50 (d, J=4.9 Hz, 2H). Compound P23 was deprotected with trifluoroacetic acid as described for t-butyl 3-hydroxyazetidine-1-carboxylate in the preparation of C19 in Example 3, before being used in the coupling step.

Workup

  1. customCompound P23 was prepared
  2. customto afford P23

Sources & evidence

ORD record
ord-80435d47129c4a7890095d335547f730
Source dataset
uspto-grants-2013_12
Patent number
US08618117B2

Reaction notes

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