Trifluoroacetic acid → HCID 10386930, compound

HRID 553562Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[CH2:17]1.C([Sn]([N:41]=[N+:42]=[N-:43])(CCCC)CCCC)CCC.C(O)(C(F)(F)F)=O>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([O:22][CH2:23][CH2:24][CH2:25][C:26]2[N:41]=[N:42][NH:43][N:27]=2)[CH2:17]1

Participants

Conditions

Temperature: 120 °C

Procedure

333 mg of (1R,3S)-4-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]butyronitrile are dissolved in 5 ml of xylene, and 919 mg of tributyltin azide are added. The mixture is stirred at 120° C. for 18 h and, after cooling, titurated with 0.5 ml of TFA. The solvent is removed under reduced pressure and the residue is purified by RP-HPLC. This gives (1R,3S)-5-{3-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]propyl}-2H-tetrazole as a colorless oil. C22H29N5O3 (411.51), MS (ESI): 412 (M+H+).

Workup

customThe solvent is removed under reduced pressure
customthe residue is purified by RP-HPLC

Sources & evidence

ORD record: ord-f9b8f58307d9471a9fe9ffcb64611a4d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048901B2

Reaction notes

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