Chloroform → HCID 72414501, compound

HRID 33993Notes

Reaction equation

HRID 33993 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[CH:38][C:6]([CH2:7][O:8][C:9](=[O:37])[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[C:28](C)(C)[O:29][SiH2]C(C)(C)C)=[O:22])=[CH:5][CH:4]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.C(Cl)(Cl)Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:37])[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[CH2:28][OH:29])=[O:22])=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8857Ethyl Acetate2×HCID 2724141Tetrabutylammonium FluorideHCID 131727082HCID 131727082, compound

Product 1

HCID 72414501HCID 72414501, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The TBDMS ether 10 (0.37 g, 0.66 mmol) in THF (20 mL) was deprotected (Method A: Bu4NF (0.8 ml, 0.8 mmol)) to give the product (flash column chromatography 80% EtOAc/20% n-hexane, then EtOAc) as a colourless oil (0.29 g, 97%). [α]D22.1−69.6° (c=0.23, CHCl3), 1H NMR (CDCl3) δ 8.72 (s, 1H), 7.76 (s, 1H), 7.34 (d, J=8.6 Hz, 2H), 6./90 (d, J=8.6 Hz, 2H), 6.80 (s, 1H), 5.10 (m, 2H), 4.40 (m, 1H), 4.30 (m, 1H), 3.92 (s, 3H), 3.83 (s, 3H), 3.80 (m, 4H), 3.7 (m, 1H), 3.58 (m, 1H), 3.45 (m, 1H), 2.15 (m, 1H), 1.90 (m, 1H), 1.70 (m, 2H). IR (neat) 3338, 2958, 2837, 1726, 1599 cm−1.

Sources & evidence

ORD record
ord-60bbb3b673ca4c0dacd6c3c0b250d3a1
Source dataset
uspto-grants-2008_09
Patent number
US07429658B2

Reaction notes

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