Trifluoroacetic acid → HCID 24902685, compound

HRID 1916255Notes

Reaction equation

HRID 1916255 reaction equation
Cl[C:2]1[CH:7]=[N: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][N:6]=[CH: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 73277ChloropyrazineHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 24902685HCID 24902685, compound

Procedure

Compound P22 was prepared according to the general procedure described for the synthesis of P21 in Preparation 21, using 2-chloropyrazine in place of 2-bromopyridine, to afford P22. LCMS (ESI) m/z 252.4 (M÷1). 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9H), 3.97 (m, 2H), 4.32 (m, 2H), 5.30 (m, 1H), 8.03 (dd, J=2.5, 1.2 Hz, 1H), 8.16 (d, J=2.5 Hz, 1H), 8.26 (d, Hz, 1H). Compound P22 was deprotected with trifluoroacetic acid as described for tert-butyl 3-hydroxyazetidine-1-carboxylate in the preparation of C19 in Example 3, before being used in the coupling step.

Workup

  1. customCompound P22 was prepared
  2. customdescribed for the synthesis of P21 in Preparation 21
  3. customto afford P22

Sources & evidence

ORD record
ord-add8cb8616514e66a9318e5d9c140c88
Source dataset
uspto-grants-2013_12
Patent number
US08618117B2

Reaction notes

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