Trifluoromethanesulfonic acid → HCID 72724108, compound

HRID 1364012Notes

Reaction equation

[C:1]([NH:4][C@@H:5]1[C@@H:10]([N:11]=[N+:12]=[N-:13])[CH2:9][C:8]([P:14]([O:19][CH2:20][CH3:21])(=[O:18])[O:15][CH2:16][CH3:17])=[CH:7][C@H:6]1[OH:22])(=[O:3])[CH3:2].ClC(Cl)(Cl)C(=N)O[CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29].C(S(O)(=O)=O)(F)(F)F>>[C:1]([NH:4][C@@H:5]1[C@@H:10]([N:11]=[N+:12]=[N-:13])[CH2:9][C:8]([P:14]([O:15][CH2:16][CH3:17])(=[O:18])[O:19][CH2:20][CH3:21])=[CH:7][C@H:6]1[O:22][CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 62406Trifluoromethanesulfonic acid2×

HCID 23643784HCID 23643784, compound

HCID 86641300HCID 86641300, compound

Product 1

HCID 72724108HCID 72724108, compoundYield 82%

Procedure

By a procedure similar to that for 11a, the reaction of alcohol 10b (498 mg, 1.5 mmol) with 3-pentyl trichloroacetimidate (420 mg, 1.8 mmol) in the presence of CF3SO3H (15.6 μL, 0.18 mmol), followed by another batches of the imidate and CF3SO3H, gave the alkylation product 11b (495 mg, 82% yield). Colorless oil; TLC (EtOAc/hexane, 1:1) Rf=0.2; [α]D20=−61.3 (c=0.65, CDCl3); IR (neat) 2100, 1756, 1634, 1246 cm−1; 1H NMR (600 MHz, CDCl3) δ 6.56 (1 H, d, JP-2=21.6 Hz), 5.71 (1 H, d, J=6.9 Hz), 4.52 (1 H, d, J=7.8 Hz), 4.34-4.30 (1 H, m), 4.11-4.01 (4 H, m), 3.31-3.23 (2 H, m), 2.69-2.64 (1 H, m), 2.12-2.08 (1 H, m), 2.01 (3 H, s), 1.51-1.43 (4 H, m), 1.39-1.31 (6 H, m), 0.90-0.81 (6 H, m); 13C NMR (150 MHz, CDCl3) δ 171.0, 141.7, 126.3 (C-1, d, JP-1=182 Hz), 810.9, 73.7, 62.14, 62.10, 54.3, 57.1, 31.0, 26.2, 25.4, 23.6, 16.4, 16.3, 9.6, 9.2; 31P NMR (162 MHz, CDCl3) δ 16.99; HRMS calcd for C17H32N4O5P (M++H): 403.2110, found: m/z 403.2111.

Sources & evidence

ORD record: ord-c7a09d3f19ca4ca0833b1ea7055c3422
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888337B2

Reaction notes

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