Dimethylformamide → HCID 67304240, compound

HRID 535104Notes

Reaction equation

F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[O:28]=[C:29]1[C@H:35]2[CH2:36][C@H:31]([CH2:32][CH2:33][C@@H:34]2[C:37]([OH:39])=O)[O:30]1.[C:40]1([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[C:40]1([N:46]2[CH2:51][CH2:50][N:49]([C:37]([C@H:34]3[CH2:33][CH2:32][C@H:31]4[CH2:36][C@@H:35]3[C:29](=[O:28])[O:30]4)=[O:39])[CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 70961-Phenylpiperazine

HCID 81531Diisopropylethylamine

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

HCID 56605004(1s,2s,5s)-7-Oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 67304240HCID 67304240, compound

Procedure

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (7.0 g, 0.016 mol) was added to a solution of (1S,2S,5S)-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid (14.4 mmol, 0.0144 mol) and 1-Phenylpiperazine (2.4 mL, 0.016 mol) in N,N-dimethylformamide (30 mL, 0.4 mol) at 0 Celsius. After 5 minutes, N,N-diisopropylethylamine (7.5 mL, 0.043 mol) was added at 0 Celsius. The mixture was stirred at RT for overnight. The product was purified by flash chromatography on silica gel column (ethyl acetate in hexanes: 60%).

Workup

customThe product was purified by flash chromatography on silica gel column (ethyl acetate in hexanes: 60%)

Sources & evidence

ORD record: ord-17e44e8e84634858a1e572e0a91f7478
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853243B2

Reaction notes

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