(R,S)-Boc-2-amino-tetradecanoic acid → tert-butyl N-[1-(hydroxymethyl)pentadecyl]carbamate

HRID 970296Notes

Reaction equation

HRID 970296 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1[N-]C(NC(OC(C)(C)C)=O)CCCCCCCCCCC)(=O)[CH3:26]>C(Cl)(Cl)Cl.CO>[OH:12][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 2756016(R,S)-Boc-2-amino-tetradecanoic acidHCID 1317267262,3,4,6-Tetra-o-acetyl-n-{1-(r/s)-[(tert-butoxycarbonyl)-amino]dodecyl}-beta-d-glucopyranosylamide

Product 1

HCID 15673748tert-butyl N-[1-(hydroxymethyl)pentadecyl]carbamateYield 82%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Procedure as for 44, Method C (using 42 in place of 41). RF=0.72 chloroform:methanol 10:0.7 (v/v); yield 82%; 1H NMR δ 3.69-3.45 (m, 2H, αCH, CH2a), 2.97 (m, 1H, CH2b), 1.41 (s, 9H, 3×Boc CH3), 1.25 (m, 18H, 13CH2), 0.88 (t, 3H, CH3); FAB MS C21H43NO3 (357.32) m/z (%) 380 [M+Na]+ (15), 258 [M−Boc+H]+ (100).

Sources & evidence

ORD record
ord-6aee1f40dd394b2baba867522ee515ed
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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