tert-Butyl bromoacetate → HCID 86664832, compound

HRID 1628270Notes

Reaction equation

HRID 1628270 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:7]=1)=[O:4].C(N(C(C)C)C(C)C)C.Br[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>CC#N>[O:4]=[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:7]=1)[C@@H:2]([NH:1][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 67496453HCID 67496453, compound

Product 1

HCID 86664832HCID 86664832, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a flask with (S)-2-amino-3-(4-fluorophenyl)-N-(3-(pyridin-4-yl)phenyl)propanamide (200 mg, 0.6 mmol) was added CH3CN as solvent, N-ethyl-N-isopropylpropan-2-amine (0.15 mL, 0.89 mmol) and tert-butyl 2-bromoacetate (0.097 mL, 0.66 mmol) and was heated at 55 degree for 5 hours. Reverse phase purification on HPLC followed by silica gel purification afforded 39 mg (15%) 34.4. 1H NMR (400 MHz, MeOH) δ ppm 8.50-8.68 (m, 2H) 7.88-7.99 (m, 1H) 7.61-7.75 (m, 2H) 7.55-7.60 (m, 1H) 7.42-7.52 (m, 2H) 7.23-7.31 (m, 2H) 6.97-7.04 (m, 2H) 3.53 (t, J=6.85 Hz, 1H) 3.29 (s, 2H) 3.05-3.12 (m, 1H) 2.95-3.03 (m, 1H) 1.43 (s, 9H)

Workup

  1. customReverse phase purification on HPLC
  2. customfollowed by silica gel purification

Sources & evidence

ORD record
ord-c18cc77a28064fd58fbce5cc17e88175
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

Loading…