Trifluoroacetic acid → racemic 2-oxo-2-phenylethyl (3R,4S)-4-allyl-3-azidopyrrolidine-3-carboxylate trifluoroacetate

HRID 61407Notes

Reaction equation

HRID 61407 reaction equation
[CH2:1]([C@H:4]1[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C@@:5]1([N:28]=[N+:29]=[N-:30])[C:16]([O:18][CH2:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH:2]=[CH2:3].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>C(Cl)Cl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH2:1]([C@H:4]1[CH2:8][NH:7][CH2:6][C@@:5]1([N:28]=[N+:29]=[N-:30])[C:16]([O:18][CH2:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131737174racemic 1-tert-butyl 3-(2-oxo-2-phenylethyl) (3R,4S)-4-allyl-3-azidopyrrolidine-1,3-dicarboxylate

Product 1

HCID 131734495racemic 2-oxo-2-phenylethyl (3R,4S)-4-allyl-3-azidopyrrolidine-3-carboxylate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While under nitrogen, a solution of racemic 1-tert-butyl 3-(2-oxo-2-phenylethyl) (3R,4S)-4-allyl-3-azidopyrrolidine-1,3-dicarboxylate (0.425 g, 1.02 mmol) in methylene chloride (4 mL) was treated with trifluoroacetic acid (1.2 mL, 15 mmol) quickly dropwise, and the resulting homogeneous mixture was stirred at room temperature. After 40 min, the mixture was concentrated under reduced pressure and dried under high vacuum for several hours to give crude racemic 2-oxo-2-phenylethyl (3R,4S)-4-allyl-3-azidopyrrolidine-3-carboxylate trifluoroacetate as a dark amber viscous oil which was used immediately in the next step. LC-MS ESI+MS found for C16H18N4O3 m/z 315.2 (M+H). 1H NMR (CDCl3, 400 MHz) δ 7.92 (m, 2 H), 7.69 (m, 1 H), 7.55 (m, 2 H), 5.75 (m, 1 H), 5.62 (m, 2 H), 5.24 (d, J=17 Hz, 1 H), 5.20 (d, J=10.2 Hz, 1 H), 4.08 (m, 1 H), 3.80 (m, 1 H), 3.55 (m, 2 H), 2.80 (m, 1 H), 2.63 (m, 1 H), 2.27 (m, 1 H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customdried under high vacuum for several hours

Sources & evidence

ORD record
ord-6fdb8bf5ec8d4827960b1a55c0de814e
Source dataset
uspto-grants-2016_09
Patent number
US09440995B2

Reaction notes

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