Methyl chloroformate → HCID 58786450, compound

HRID 1376039Notes

Reaction equation

HRID 1376039 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.O.[OH-].[Na+].Cl[C:34]([O:36][CH3:37])=[O:35]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[CH2:15][NH:16][C:34]([O:36][CH3:37])=[O:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 21881883Oxolane--water (1/1)HCID 58786473HCID 58786473, compound

Product 1

HCID 58786450HCID 58786450, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4-[2-Amino-1-(2,4-difluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (209) (0.38 g, 1.13 mmol) in a 1:1 mixture of THF/H2O (30 mL) was added NaOH (0.05 g, 1.24 mmol) and methyl chloroformate (0.11 g, 1.13 mmol ). The reaction was allowed to stir at room temperature for 2 h. The reaction mixture was then diluted with EtOAc (200 mL) and washed with H2O (100 mL) and brine (100 mL). The organic phase was concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 50% hexanes/50% EtOAc) yielding 0.23 g (50%) pure product.

Workup

  1. washwashed with H2O (100 mL) and brine (100 mL)
  2. concentrationThe organic phase was concentrated to dryness
  3. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 50% hexanes/50% EtOAc)

Sources & evidence

ORD record
ord-8fa0fdd583f045679efbe10d6dee89e2
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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