Dimethylformamide → dimethyl(2S,3S,5S)-5-(2-oxo-2-pyrrolidin-1-ylethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 61465Notes

Reaction equation

HRID 61465 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C@H:10]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[C@@H:9]([C:25]([O:27][CH3:28])=[O:26])[CH2:8][C@H:7]([O:29][CH2:30][C:31]([OH:33])=O)[CH2:6]1)=[O:4].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[O:33]=[C:31]([N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)[CH2:30][O:29][C@@H:7]1[CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[C@H:10]([C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:12])[C@@H:9]([C:25]([O:27][CH3:28])=[O:26])[CH2:8]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67305595((3s,5s,6s)-1,5-Bis(methoxycarbonyl)-6-[(4-phenylpiperazin-1-yl)carbonyl]piperidin-3-yloxy)acetic acid

Product 1

HCID 67304375dimethyl(2S,3S,5S)-5-(2-oxo-2-pyrrolidin-1-ylethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ((3S,5S,6S)-1,5-bis(methoxycarbonyl)-6-[(4-phenylpiperazin-1-yl)carbonyl]piperidin-3-yloxy)acetic acid (57 mg, 0.00012 mol), pyrrolidine (0.0308 mL, 0.000369 mol), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (163 mg, 0.000369 mol) in N,N-dimethylformamide (0.50 mL, 0.0064 mol) was added N,N-diisopropylethylamine (0.0857 mL, 0.000492 mol). The mixture was stirred at rt for 2 h, then diluted with ethyl acetate, washed with water, brine and dried. After concentrated to dry, the residue was used directly in next step.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationAfter concentrated
  4. customto dry

Sources & evidence

ORD record
ord-efed2664252b42bb8626b707365e3933
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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