Tetrahydrofuran → HCID 66662137, compound

HRID 2275627Notes

Reaction equation

HRID 2275627 reaction equation
N(C(OCC)=O)=NC(OCC)=O.FC(F)(F)C(O)=O.[OH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:32]=[CH:31][C:30]([C:33]3([C:36]([N:38]4[CH2:42][CH2:41][C@@:40]5([C:46]6[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=6[C:44](=[O:51])[O:43]5)[CH2:39]4)=[O:37])[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.[N:52]1[CH:57]=[CH:56][C:55](O)=[CH:54][CH:53]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>>[N:52]1[CH:57]=[CH:56][C:55]([O:20][CH:21]2[CH2:22][CH2:23][N:24]([C:27]3[N:32]=[CH:31][C:30]([C:33]4([C:36]([N:38]5[CH2:42][CH2:41][C@@:40]6([C:46]7[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=7[C:44](=[O:51])[O:43]6)[CH2:39]5)=[O:37])[CH2:34][CH2:35]4)=[CH:29][CH:28]=3)[CH2:25][CH2:26]2)=[CH:54][CH:53]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66661981HCID 66661981, compoundHCID 178418642HCID 178418642, compound

Product 1

HCID 66662137HCID 66662137, compound

Procedure

Diethyl azodicarboxylate (3.0×10−1 μL, 0.00019 mol) was added to a mixture of (1R)-1′-({1-[6-(4-hydroxypiperidin-1-yl)pyridin-3-yl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one trifluoroacetate (salt) (42 mg, 0.000077 mol, example 172), 4-pyridinol (18 mg, 0.00019 mol) and triphenylphosphine (5.0×10−1 mg, 0.00019 mol) in tetrahydrofuran (1.0 mL, 0.012 mol). The reaction mixture was stirred at room temperature overnight. The crude product was purified by prep-LCMS. LC/MS: 511.2 (M+H+).

Workup

  1. customThe crude product was purified by prep-LCMS

Sources & evidence

ORD record
ord-b5724d7e22e9456b86a9d0ce62cbff14
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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