1,2-Dichloroethane → HCID 69465211, compound

HRID 1157143Notes

Reaction equation

[C:1]1([C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:19](O)=[O:20])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[C:22]([O:26][C:27](=[O:35])[CH2:28][CH:29]([NH2:34])[CH:30]([OH:33])[CH2:31][F:32])([CH3:25])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C1COCC1>[C:22]([O:26][C:27](=[O:35])[CH2:28][CH:29]([NH:34][C:19]([CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][N:13]1[C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1)=[O:12])=[O:20])[CH:30]([OH:33])[CH2:31][F:32])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of (S)-1-(isoquinoline-1-carbonyl)-2-piperidinecarboxylic acid (278 mg, 0.98 mmol), 3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (213 mg, 1.03 mmol), HOBt (145 mg, 1.07 mmol), DMAP (137 mg, 1.12 mmol) and anhydrous THF (25 ml) was cooled to 0° C. then EDC (206 mg, 1.07 mmol) was added. The mixture was allowed to warm to room temperature during 16 hrs then concentrated under reduced pressure. The residue was purified by flash chromatography (5% methanol in DCM) to afford the title compound as a white foam (425 mg, 92%): 1H NMR (400 MHz, CDCl3) δ 1.20-3.30 (17H, m), 3.95-4.18 (2H, m), 4.29-4.64 (4H, m), 4.86-5.01 (1H, m), 7.65-8.00 (4H, m), 8.10-9.00 (3H, m); 19F (376 MHz, CDCl3) δ −229.39, −229.41, −229.57, −229.60, −229.64, −229.69, −230.41, −231.08.

Workup

temperatureto warm to room temperature during 16 hrs
concentrationthen concentrated under reduced pressure
customThe residue was purified by flash chromatography (5% methanol in DCM)

Sources & evidence

ORD record: ord-a34eb20cb8d74b82b3992420768e775a
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807659B2

Reaction notes

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