Ethyl chloroformate → 5-Ethoxycarbonylamino-2-(3(S)-(t-butoxycarbonyl)aminopyrrolidin 1-yl)fluorobenzene

HRID 8161Notes

Reaction equation

HRID 8161 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[C:6]([F:8])[CH:7]=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>N1C=CC=CC=1>[CH2:26]([O:25][C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[C:6]([F:8])[CH:7]=1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 20725689HCID 20725689, compound

Product 1

HCID 207256915-Ethoxycarbonylamino-2-(3(S)-(t-butoxycarbonyl)aminopyrrolidin 1-yl)fluorobenzene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-2-(3(S)-(t-butoxycarbonyl)aminopyrrolidin-1-yl)fluorobenzene (30.4 g, 0.103 M) was dissolved in dry pyridine (150 ml) and cooled under nitrogen with stirring to 0°. Ethyl chloroformate (12.3, 0.113 M) was added dropwise, and the mixture stirred 1 hour at the same temperature. Ice-water (250 ml) was added, and stirring continued for 1 hour. The resulting precipitate was collected, washed thoroughly with water, and air dried. The residue was treated with toluene, azeotroped to half volume, then treated with isohexane (500 ml), to precipitate the desired product (35.3 g).

Workup

  1. temperaturecooled under nitrogen
  2. stirringthe mixture stirred 1 hour at the same temperature
  3. stirringstirring
  4. customThe resulting precipitate was collected
  5. washwashed thoroughly with water, and air
  6. customdried
  7. additionThe residue was treated with toluene
  8. customazeotroped to half volume
  9. additiontreated with isohexane (500 ml)
  10. customto precipitate the desired product (35.3 g)

Sources & evidence

ORD record
ord-d7fabcc4ef964da58ab368502f8f1aa2
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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