HCID 178451925, compound → HCID 178451923, compound

HRID 2273050Notes

Reaction equation

HRID 2273050 reaction equation
C(OC([NH:11][CH:12]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([C@@H:27]4[CH2:31][CH2:30][CH2:29][N:28]4[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:25][CH:26]=3)=[CH:18][CH:17]=2)[CH2:13]1)=O)C1C=CC=CC=1>C(O)(=O)C.Br>[NH2:11][CH:12]1[CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([C@@H:27]4[CH2:31][CH2:30][CH2:29][N:28]4[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:25][CH:26]=3)=[CH:18][CH:17]=2)[CH2:15]1

Participants

4

Reactant 1

HCID 178451925HCID 178451925, compound

Product 1

HCID 178451923HCID 178451923, compoundYield 140.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

To a suspension of A8 (17.8 g) in acetic acid (250 mL), hydrogen bromide (33% in acetic acid, 25 mL) was added dropwise at rt. After stirring for an additional hour, the reaction was filtered though a pad of CELITE™454, washed with ethyl acetate, concentrated to afford the crude product, which was purified by silica gel flash column chromatography (Hexanes/EtOAc=3/1 (v/v)) to provide A9 (18.5 g).

Workup

  1. additionwas added dropwise at rt
  2. filtrationthe reaction was filtered though a pad of CELITE™454
  3. washwashed with ethyl acetate
  4. concentrationconcentrated
  5. customto afford the crude product, which
  6. customwas purified by silica gel flash column chromatography (Hexanes/EtOAc=3/1 (v/v))

Sources & evidence

ORD record
ord-cd7304df22f2491bab3c1f078304d156
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

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