HCID 10867840, compound → HCID 10880397, compound

HRID 1669921Notes

Reaction equation

HRID 1669921 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:15])([CH2:13][F:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:11][C:10](=[O:12])[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([CH3:15])[CH2:13][F:14])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 10867840HCID 10867840, compound

Product 1

HCID 10880397HCID 10880397, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N-Boc acid 2 (767 mg, 3.46 mmol) in 10 mL of dry CH2Cl2 was stirred overnight with 3 eq of tert-butyl-2,2,2-tricholoracetimdate (2.27 g). After concentration under reduced pressure, the crude product was purified by silica gel column chromatography (5% EtOAc in hexane) to provide 3 (510 mg, 53%) as a white solid: mp 41-42 EC (EtOAc/hexane); 1H NMR (CDCl3) δ 1.44 (9H, s), 1.47 (3H, d, J=2.4), 1.48 (9H, s), 4.57-4.85 (2H, m), 5.34 (1H, broad s). Anal. (C13H24FNO4) C, H, N.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe crude product was purified by silica gel column chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-185c055e8f794532b39337cb8e1a4d49
Source dataset
uspto-grants-2011_08
Patent number
US07989649B2

Reaction notes

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