HCID 59145557, compound → HCID 59145585, compound

HRID 919107Notes

Reaction equation

HRID 919107 reaction equation
[NH2:1][CH2:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][NH:8][C@H:9]([C:16]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])[CH2:10][O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.[CH:26]([C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]([NH:38][O:39]C(OCC(C)C)C)=[O:37])=[CH:30][CH:29]=1)=O>ClCCCl>[C:12]([O:11][CH2:10][C@@H:9]([C:16]([O:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1)=[O:17])[NH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][CH2:26][C:28]2[CH:29]=[CH:30][C:31](/[CH:34]=[CH:35]/[C:36]([NH:38][OH:39])=[O:37])=[CH:32][CH:33]=2)=[CH:25][CH:24]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 59145557HCID 59145557, compoundHCID 59145591HCID 59145591, compound

Product 1

HCID 59145585HCID 59145585, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of cyclopentyl N-[4-(aminomethyl)benzyl]-O-tert-butyl-L-serinate (prepared as described in Example 73—0.282 g, 0.67 mmol) and (2E)-3-(4-formylphenyl)-N-(1-isobutoxyethoxy)acrylamide (prepared as described in Example 12—0.230 g, 0.79 mmol) in DCE (25 mL) was added STAB (0.700 g, 3.3 mmol). The mixture was stirred at RT for 3 h, and then quenched with sat. NaHCO3 solution (75 mL). The product was then extracted with DCM (3×100 mL) and the combined organic extracts were dried (MgSO4), concentrated and purified by preparative HPLC to yield the desired product (5 mg, 2%). LCMS purity 98%, m/z=524.25 [M+H]+, 1H NMR (300 MHz, CD3OD) δ: 7.41 (2H, d, J=7.9 Hz), 7.24 (2H, d, J=7.7 Hz), 7.20 (3H, br s), 6.37 (1H, d, J=15.6 Hz), 5.09 (1H, t, J=5.7 Hz), 3.44-3.75 (8H, m), 3.25 (1H, t, J=3 Hz), 1.45-1.90 (8H, m), 1.04 (9H, s).

Workup

  1. additionwas added STAB (0.700 g, 3.3 mmol)
  2. customquenched with sat. NaHCO3 solution (75 mL)
  3. extractionThe product was then extracted with DCM (3×100 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a07f127a1b7b4b91924718de10ff1f8f
Source dataset
uspto-grants-2016_03
Patent number
US09273003B2

Reaction notes

Loading…