Pentafluorophenol → HCID 54012931, compound

HRID 2185509Notes

Reaction equation

HRID 2185509 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:15]([C:25]([OH:27])=[O:26])[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]1[C:34](O)=[C:33]([F:36])[C:32]([F:37])=[C:31]([F:38])[C:30]=1[F:39]>CCOC(C)=O>[F:28][C:29]1[C:34]([O:26][C:25](=[O:27])[C@@H:15]2[CH2:14][C@@H:13]([NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:17][N:16]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:33]([F:36])[C:32]([F:37])=[C:31]([F:38])[C:30]=1[F:39]

Participants

4

Reactant 2

HCID 13041PentafluorophenolHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline

Product 1

HCID 54012931HCID 54012931, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

trans-4-(N-tert-Butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline (1.96 g, 5.06 mmol) was dissolved in EtOAc (40 mL) and pentafluorophenol (PFP) (1.03 g, 5.6 mmol) was added in one portion. (1,3-)dicyclohexylcarbodiimide (DCC 1.15 g, 5.6 mmol) was pre-dissolved in EtOAc (10 mL) and added dropwise over 1 minute. A white precipitate immediately formed which, upon stirring for 1 hour, 1:5 was filtered and the filtrate was concentrated to dryness to reveal the title compound in 95% yield.

Workup

  1. additionadded dropwise over 1 minute
  2. customA white precipitate immediately formed which
  3. filtration1:5 was filtered
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-0dc9271520834badb03419135b03d8b0
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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