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Chloroacetic Acid → (3S,4R)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-(2-chloroacetoxy)pyrrolidine-1-carboxylate

HRID 1670620
Notes
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Reaction equation

HRID 1670620 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]2[C@@H:13]([OH:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[C:4]([N+:22]([O-:24])=[O:23])[CH:3]=1.[Cl:25][CH2:26][C:27](O)=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]2[C@H:13]([O:14][C:27](=[O:28])[CH2:26][Cl:25])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:10]2)=[C:4]([N+:22]([O-:24])=[O:23])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 67333783(3S,4S)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86631935(3S,4R)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-(2-chloroacetoxy)pyrrolidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (3S,4S)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylate (2.50 mmol, 1.0 g), chloroacetic acid (3.0 mmol, 300 mg) and triphenylphosphine (3.0 mmol, 850 mg) in tetrahydrofuran (40 mL) add diethylazodicarboxylate (3.0 mmol, 600 mg) and stir at room temperature for 12 h. Remove the solvent, add ethyl acetate (50 mL) to the residue and wash with water and brine. Dry over anhydrous sodium sulfate and evaporate. Purify the residue by column chromatography, eluting with 20% ethyl acetate in methylene chloride to obtain the title compound as a yellow solid (1.10 g, 98%). 1H NMR (500 MHz, CDCl3) δ 8.35 (s, 1H), 8.20 (m, 1H), 7.60 (m, 1H), 6.82 (m, 1H), 5.55 (d, J=6.8 Hz, 1H), 4.32 (m, 1H), 4.13 (bd, J=8.2 Hz, 2H), 3.90 (m, 1H), 3.79 (m, 1H), 3.74 (dd, J=4.2, 10.4 Hz, 1H), 3.25 (t, J=7.20 Hz, 1H), 1.41 (s, 9H).

Workup

  1. customRemove the solvent
  2. additionadd ethyl acetate (50 mL) to the residue
  3. washwash with water and brine
  4. dry with materialDry over anhydrous sodium sulfate
  5. customevaporate
  6. customPurify the residue by column chromatography
  7. washeluting with 20% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-ed463b4db4854657ad6f62a7d5cafb0f
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07994164B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes