Water → 1-(1,1-Dimethylethyl) (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate

HRID 2185401Notes

Reaction equation

HRID 2185401 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].N1C2C(=CC=CC=2)C=C(N[C:16](=[O:40])[C@@H:17]2[CH2:21][C@H:20](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:19][N:18]2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])C=1.[OH2:41]>CN(C)C=O>[N:1]([C@H:20]1[CH2:19][N:18]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[C@H:17]([C:16]([OH:40])=[O:41])[CH2:21]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 88192207N-tert-Butoxycarbonyl-cis-4-p-Toluenesulfonyloxy-L-Proline 3-Quinolylamide

Product 1

HCID 148426211-(1,1-Dimethylethyl) (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (206 mg) was added to a stirred solution of N-tert-butoxycarbonyl-cis-4-p-toluenesulfonyloxy-L-proline 3-quinolylamide (C, 805 mg) in N,N-dimethylformamide (8 mL)-water (1.5 mL). After sting at 70° C. for 4 hr, the solvents were removed in vacuo. The residue was diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=1:1 to 1:2, v/v) to afford the title compound (532 mg) as a pale yellow sticky oil: 1H NMR (400 MHz, CD3OD) δ 1.3-1.5 (m, 9H), 2.32 (m, 1H), 2.47 (m, 1H), 3.63 (m, 1H), 3.72 (m, 1H), 4.38 (m, 1H), 4.48 (m, 1H), 7.60 (m, 1H), 7.69 (m, 1H), 7.90 (m, 1H), 7.98 (m, 1H), 8.72-8.75 (m, 1H), and 8.92-8.93 (m, 1H).

Workup

  1. customthe solvents were removed in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-42acff798cfd4fa89d2c08070902b228
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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