Carbon tetrabromide → HCID 68528772, compound

HRID 2247665Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[O:17][C:18]4[CH2:24][CH2:23][CH2:22][CH:21](O)[C:19]=4[CH:20]=3)[N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:51]1[CH2:54][CH:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:52]1.C(N(CC)C(C)C)(C)C>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[O:17][C:18]4[CH2:24][CH2:23][CH2:22][CH:21]([N:51]5[CH2:54][CH:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:52]5)[C:19]=4[CH:20]=3)[N:12]=2)=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 5

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 81531Diisopropylethylamine

HCID 44828820Ethyl azetidine-3-carboxylate hydrochloride

HCID 68525595HCID 68525595, compound

Product 1

HCID 68528772HCID 68528772, compound

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 1 (1f) using 2-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-4,5,6,7-tetrahydro-1-benzofuran-4-ol (0.15 g, 0.45 mmol) that was obtained in Example 7 (7e), carbon tetrabromide (0.30 g, 0.90 mmol), triphenylphosphine (0.24 g, 0.90 mmol), ethyl 3-azetidinecarboxylate hydrochloride (0.11 g, 0.68 mmol), and N,N-diisopropylethylamine (0.20 ml, 1.1 mmol). Subsequently, the crude product of the title compound thus obtained was purified by thin layer chromatography on a silica gel plate using a mixed solvent of ethyl acetate and hexane (4:3) as the developing solvent to afford the title compound (27 mg) in a yield of 13% as a white crystalline solid.

Workup

customthe similar reaction to

Sources & evidence

ORD record: ord-1e9dd661db6843afa3bef2f6437c5b51
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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