Acetic Acid → HCID 71547234, compound

HRID 1184555Notes

Reaction equation

HRID 1184555 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][C@@H:8]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)(=[O:13])=[O:12])[CH2:9][C@@H:2]12.[CH2:24]([CH:26]([CH2:29][CH3:30])[CH:27]=O)[CH3:25].C(O)(=O)C.C([BH3-])#N>CO>[CH2:24]([CH:26]([CH2:29][CH3:30])[CH2:27][N:6]1[CH2:5][CH2:4][N:3]2[CH2:7][C@@H:8]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=3)(=[O:13])=[O:12])[CH2:9][C@H:2]2[CH2:1]1)[CH3:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73592-EthylbutyraldehydeHCID 498716Cyano-borohydrideHCID 71547802HCID 71547802, compound

Product 1

HCID 71547234HCID 71547234, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of Example 42 (35 mg, 0.1 mmol) in methanol (0.5 mL) was added a solution of 2-ethylbutanal (20 mg, 0.2 mmol) in methanol (0.5 mL). To this solution was added acetic acid (30 μL, 0.5 mmol) followed by MP-cyanoborohydride resin (136 mg). The resulting mixture was shaken at 50° C. overnight and then filtered. The filtrate was concentrated. The residue was dissolved in 1:1 methanol:dimethyl sulfoxide and purified by HPLC (Gilson®, Xbridge™ 50×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/acetonitrile, UV=220 nm) to afford the title compound. 1H NMR (500 MHz, pyridine-d5/D2O) δ ppm 0.82 (t, 6 H, J=7.48 Hz), 1.24-1.36 (m, 4 H), 1.42-1.54 (m, 2 H), 1.83-1.91 (m, 1 H), 2.14-2.29 (m, 6 H), 2.36 (m, 1H), 2.84 (m, 2H), 2.93 (s, 1 H), 3.01 (m, 1H), 4.21 (m, 1H), 7.67 (t, 1H, J=8 Hz), 7.85 (d, 1H, J=8 Hz), 8.36 (d, 1H, J=8 Hz), 8.48 (s, 1 H), 10.02 (d, 1H, J=8 Hz); MS (ESI) m/z 434 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionThe residue was dissolved in 1:1 methanol
  4. customdimethyl sulfoxide and purified by HPLC (Gilson®, Xbridge™ 50×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/acetonitrile, UV=220 nm)

Sources & evidence

ORD record
ord-76a4086149874a88ab2e6d1333779c06
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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