Phosgene → HCID 67310714, compound

HRID 2353437Notes

Reaction equation

HRID 2353437 reaction equation
[NH2:1][C@H:2]1[C@@H:6]([NH2:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.C(N(CC)CC)C.[C:22](Cl)(Cl)=[O:23]>ClCCl>[O:23]=[C:22]1[NH:1][CH:2]2[CH2:3][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH:6]2[NH:7]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 20677776(3R,4S)-rel-1-Boc--3,4-diaMinopyrrolidine

Product 1

HCID 67310714HCID 67310714, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl cis-3,4-diaminopyrrolidine-1-carboxylate (the product in Intermediate 11, Step C; 140 mg) and triethylamine (0.29 mL) in dichloromethane (10 mL) was added phosgene (20% in benzene, 0.4 mL) at 0° C. and the reaction mixture allowed to warm up to room temperature. The solution was evaporated after stirring for one h and purified on a Biotage Horizon® system (silica gel, 10-20% gradient of methanol containing 10% ammonium hydroxide in dichloromethane). The tert-butyl 2-oxohexahydropyrrolo[3,4-d]imidazole-5(1H)-carboxylate obtained was dissolved in trifluoroacetic acid/dichloromethane (2 mL, 1:1) and eluted through Strata-X-C™ ion exchange resin. The desired product was eluted with a solution of concentrated ammonium hydroxide in methanol (5%) and evaporated under reduced pressure.

Workup

  1. customThe solution was evaporated
  2. custompurified on a Biotage Horizon® system (silica gel, 10-20% gradient of methanol containing 10% ammonium hydroxide in dichloromethane)

Sources & evidence

ORD record
ord-25aeb22a239b4b8fb9f2aba6b49ac1a7
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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