1,2-Dichloroethane → HCID 58674952, compound

HRID 1809482Notes

Reaction equation

HRID 1809482 reaction equation
[C:1]([NH:9][C:10]1[C:11](=[O:27])[N:12]([C@@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17](O)=[O:18])[CH:13]=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([O:32][C:33](=[O:41])[CH2:34][CH:35]([NH2:40])[CH:36]([OH:39])[CH2:37][F:38])([CH3:31])([CH3:30])[CH3:29].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C1COCC1>[C:28]([O:32][C:33](=[O:41])[CH2:34][CH:35]([NH:40][C:17](=[O:18])[C@@H:16]([N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:11]1=[O:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:36]([OH:39])[CH2:37][F:38])([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 108566723-Amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl esterHCID 58674959HCID 58674959, compound

Product 1

HCID 58674952HCID 58674952, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of (S)-2-(3-benzoylamino-2-oxo-2H-pyridin-1-yl)-3-phenyl-propionic acid (2.20 g, 6.07 mmol), 3(R,S)-Amino-5-fluoro-4(R,S)-hydroxy-pentanoic acid tert-butyl ester (1.39 g, 6.68 mmol), HOBt (902 mg, 6.68 mmol), DMAP (853 mg, 6.98 mmol) and THF (20 mL) was cooled to 0° C. then EDC (1.28 mg, 6.68 mmol) was added. The mixture was allowed to warm to room temperature during 16 h then concentrated under reduced pressure. The residue was purified by flash chromatography (30-70 to 55-45% ethyl acetate/hexane) to afford the title compound as a white foam (1.23 g, 32%); 1H NMR (400 MHz, CDCl3) δ 0.88-0.93 (3H, m), 1.35-1.42 (9H, 2s), 2.50-2.65 (2H, m), 3.20-3.35 (2H, m), 3.60 (1H, m), 3.98 (1H, m), 4.10-4.32 (3H, m), 5.62-5.70 (1H, m), 6.44 (1H, m), 6.80-6.98 (1H, m), 7.21-7.41 (5H, m), 7.55-7.62 (3H, m), 7.95 (2H, m), 8.58 (1H, t), 9.18 (1H, br s).

Workup

  1. temperatureto warm to room temperature during 16 h
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (30-70 to 55-45% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-234a856835af4546a3d099a0f6d14ae8
Source dataset
uspto-grants-2013_01
Patent number
US08362043B2

Reaction notes

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