Triphosgene → (2R,4S)-5-biphenyl-4-yl-4-isocyanato-2-methyl-pentanoic acid benzyl ester

HRID 2384026Notes

Reaction equation

HRID 2384026 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.Cl.[CH2:14]([O:21][C:22](=[O:41])[C@H:23]([CH3:40])[CH2:24][C@H:25]([NH2:39])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[CH2:14]([O:21][C:22](=[O:41])[C@H:23]([CH3:40])[CH2:24][C@H:25]([N:39]=[C:2]=[O:4])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:31][CH:32]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 67505899HCID 67505899, compound

Product 1

HCID 86648208(2R,4S)-5-biphenyl-4-yl-4-isocyanato-2-methyl-pentanoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred 1:1 mixture of methylene chloride/8% aqueous NaHCO3 (6 mL) at 0° C. is added triphosgene (18 mg, 0.061 mmol). After stirring the mixture at 0° C. for 5 minutes, (2R,4S)-4-amino-5-biphenyl-4-yl-2-methyl-pentanoic acid benzyl ester hydrochloride (75 mg, 0.183 mmol) is added and stirring is continued for 15 minutes. The organic phase is separated and dried over sodium sulfate. The solvent is removed under reduced pressure to furnish (2R,4S)-5-biphenyl-4-yl-4-isocyanato-2-methyl-pentanoic acid benzyl ester.

Workup

  1. stirringAfter stirring the mixture at 0° C. for 5 minutes
  2. stirringstirring
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-0c485a2c094943a9927d1815dad7d314
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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