Tert-Butylamine → 2-{4-[(1-Carboxy-ethoxy)-hydroxy-phosphoryl]-but-2-enyl}-6-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid 2-trimethylsilanyl-ethyl Ester

HRID 272134Notes

Reaction equation

HRID 272134 reaction equation
[CH3:1][Si:2]([CH3:51])([CH3:50])[CH2:3][CH2:4][O:5][C:6](=[O:49])[CH:7]([CH2:33][CH:34]=[CH:35][CH2:36][P:37]([O:41][CH:42]([C:44]([O:46]CC)=[O:45])[CH3:43])([O:39]C)=[O:38])[CH2:8][C:9]([CH3:32])=[CH:10][CH2:11][C:12]1[C:13]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[C:14]2[C:18](=[C:19]([CH3:23])[C:20]=1[O:21][CH3:22])[CH2:17][O:16][C:15]2=[O:24].C(N)(C)(C)C>>[CH3:50][Si:2]([CH3:1])([CH3:51])[CH2:3][CH2:4][O:5][C:6](=[O:49])[CH:7]([CH2:33][CH:34]=[CH:35][CH2:36][P:37]([O:41][CH:42]([C:44]([OH:46])=[O:45])[CH3:43])([OH:39])=[O:38])[CH2:8][C:9]([CH3:32])=[CH:10][CH2:11][C:12]1[C:13]([O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])=[C:14]2[C:18](=[C:19]([CH3:23])[C:20]=1[O:21][CH3:22])[CH2:17][O:16][C:15]2=[O:24]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 765410252-{4-[(1-Ethoxycarbonyl-ethoxy)-methoxy-phosphoryl]-but-2-enyl}-6-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid 2-trimethylsilanyl-ethyl Ester

Product 1

HCID 765461932-{4-[(1-Carboxy-ethoxy)-hydroxy-phosphoryl]-but-2-enyl}-6-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid 2-trimethylsilanyl-ethyl Ester

Procedure

A solution of 2-{4-[(1-ethoxycarbonyl-ethoxy)-methoxy-phosphoryl]-but-2-enyl}-6-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid 2-trimethylsilanylethyl ester (12 mg, 0.016 mmol) in tert-butylamine (1 mL, 9.6 mmol) was heated at 65° C. for 16 hours. The solution was allowed to cool down to room temperature and concentrated to provide the crude product as an oil. 1H NMR (300 MHz, CDCl3) 0.03 (s, 9H), 0.04 (s, 9H), 0.86-0.98 (m, 2H), 1.22-1.33 (m, 2H), 1.50 (d, 3H, J=7 Hz), 1.78 (s, 3H), 2.05-2.30 (m, 4H), 2.10 (s, 3H), 2.48-2.63 (m, 3H), 3.40 (d, 2H, J=7 Hz), 3.76 (s, 3H), 4.08 (appt t, 2H, J=9 Hz), 4.25-4.33 (m, 2H), 4.75-4.84 (m, 1H), 5.13 (s, 2H), 5.15-5.23 (m, 1H), 5.33-5.55 (m, 2H); 31P (121.4 MHz, CDCl3) δ 28.9; MS (m/z) 725.3 [M−H]−.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-472a4483b77e4769ac59369c9bbd2a62
Source dataset
uspto-grants-2008_11
Patent number
US07452901B2

Reaction notes

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