Ethanol → Diethyl[[[tris(4-methoxyphenyl)methyl]oxy]methyl][[[[bis(1-methylethyl)amino](ethoxy)phosphino]oxy]methyl]propanedioate

HRID 2417148Notes

Reaction equation

HRID 2417148 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([C:7]([O:24][CH2:25][C:26]([CH2:37][OH:38])([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(N([P:48]([N:53]([CH:57]([CH3:59])[CH3:58])[CH:54]([CH3:56])[CH3:55])([O-:52])([O-])OCl)C(C)C)(C)C.[CH2:60](O)[CH3:61]>C(OCC)(=O)C.CCCCCC.C(N(CC)CC)C>[CH2:35]([O:34][C:32](=[O:33])[C:26]([CH2:25][O:24][C:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:40][CH:39]=1)[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)([CH2:37][O:38][P:48]([N:53]([CH:54]([CH3:55])[CH3:56])[CH:57]([CH3:58])[CH3:59])[O:52][CH2:60][CH3:61])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:36]

Participants

5

Reactant 3

HCID 702EthanolHCID 15539820Diethyl 2-[(4,4',4''-trimethoxytrityl)oxymethyl]-2-hydroxymethylmalonateHCID 131724663Chloro bis[(n,n,-diisopropyl)amino]phosphite

Product 1

HCID 69928486Diethyl[[[tris(4-methoxyphenyl)methyl]oxy]methyl][[[[bis(1-methylethyl)amino](ethoxy)phosphino]oxy]methyl]propanedioateYield 91%

Reagents, catalysts & solvents 1

HCID 22141343EtOAc hexane triethylamineSolvent

Procedure

Compound 4 was prepared from 1 (553 mg, 1.0 mmol), chloro bis[(N,N,-diisopropyl)amino]phosphite (307 mg, 1.15 mmol), and ethanol (69 mg, 1.5 mmol) as described for 3. Isolation on a silica gel column using gradient from 5:93:2 to 40:58:2 ethyl acetate/hexane/triethylamine gave 4 (662 mg, 91%) as a colorless oil. HR FAB MS: found m/z 727.3486; C39H54NO10P requires 727.3485. 1H NMR (CDCl3) δ 7.40-7.27 (6H, m), 6.92-6.67 (6H, m), 4.37 (1H, dd, J=5.8 and 7.5 Hz), 4.26-4.02 (5H, m), 3.77 (9H, s), 3.68 (2H, s), 3.75-3.39 (2H, m), 3.20 (2H, m), 1.40-1.00 (21H, m). 13C NMR (CDCl3) δ 168.6 (C), 168.4 (C), 158.3 (C), 136.5 (C), 130.0 (CH), 113.0 (CH), 85.6 (C), 63.7 (CH2), 61.6 (CH2), 61.3 (CH2), 60.9 (CH2), 60.0 (CH2), 58.9 (C), 55.2 (CH3), 43.0 (CH), 42.8 (CH), 24.6 (CH3), 24.4 (CH3), 19.1 (CH3), 14.0 (CH3). 31P NMR (CDCl3) δ 145.6.

Sources & evidence

ORD record
ord-51f628b3aad14624892ce700773f9316
Source dataset
uspto-grants-2004_11
Patent number
US06825338B2

Reaction notes

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