(R,S)-Boc-2-amino-tetradecanoic acid → 2-(t-Butoxycarbonylamino)dodecanol

HRID 970297Notes

Reaction equation

HRID 970297 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]CC)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(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)C>CCCCCC.C(OCC)(=O)C>[OH:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

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 156737502-(t-Butoxycarbonylamino)dodecanolYield 87%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Procedure as for 44 (using 40 in place of 41). RF=0.50 hexane:ethyl acetate 4:1 (v/v); yield 87%; 1H NMR δ 3.65-3.48 (m, 3H, αCH, CH2), 1.43 (s, 9H, 3×Boc CH3), 1.24 (m, 18H, 9CH2), 0.86 (t, 3H, CH3); FAB MS C17H35NO3 (301.46) m/z (%) 302 [M+H]+ (15), 324 [M+Na]+ (5), 434 [M+Cs]+ (10), 202 [M−Boc+H]+ (95).

Sources & evidence

ORD record
ord-1558021506d94a2e9e99ed3df0dda994
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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