Pyridine → HCID 178472148, compound

HRID 910554Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:42])[CH:5]([N:7]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[PH:8]([CH2:10][C:11]([CH3:34])=[CH:12][CH2:13][C:14]1[C:15]([O:27]CC[Si](C)(C)C)=[C:16]2[C:20](=[C:21]([CH3:25])[C:22]=1[CH2:23][CH3:24])[CH2:19][O:18][C:17]2=[O:26])=[O:9])[CH3:6])[CH3:2].N1C=CC=CC=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:42])[CH:5]([N:7]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[PH:8]([CH2:10][C:11]([CH3:34])=[CH:12][CH2:13][C:14]1[C:15]([OH:27])=[C:16]2[C:20](=[C:21]([CH3:25])[C:22]=1[CH2:23][CH3:24])[CH2:19][O:18][C:17]2=[O:26])=[O:9])[CH3:6])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

2-({4-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phenoxy-phosphinoylamino)-propionic acid ethyl ester (7.5 mg, 0.012 mmol) was dissolved in TFA/DCM (10%, 0.3 mL) at −20° C. The reaction mixture was warmed to 0° C. and stirred at this temperature for 45 minutes. Pyridine (0.09 mL) was added the solvents were removed in vacuo. The crude material was purified by RP-HPLC (eluent: water/MeCN). The product-containing fractions were combined and lyophilized, yielding a white powder (5.5 mg, 87%). 1H NMR (300 MHz, CDCl3): δ=1.12-1.29 (m, 6H), 2.03 (s, 3H), 2.17 (s, 3H), 2.65-2.74 (m, 4H), 3.38 (m, 1H), 3.53 (t, J=6.3 Hz, 2H), 4.03 (m, 3H), 5.22 (s, 2H), 5.36 (m, 1H), 7.11-7.16 (m, 3H), 7.24-7.30 (m, 2H), 7.72 (m, 1H) ppm; 31P NMR (121 MHz, CDCl3): δ=27.11, 27.57 ppm; MS=515 [M++1].

Workup

customwere removed in vacuo
customThe crude material was purified by RP-HPLC (eluent: water/MeCN)

Sources & evidence

ORD record: ord-4bd032c2bf2f4621a58e40e471030765
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022083B2

Reaction notes

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