Ethanamine, 2,2,2-trifluoro- → HCID 71623152, compound

HRID 390771Notes

Reaction equation

HRID 390771 reaction equation
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([OH:21])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[F:55][C:56]([F:60])([F:59])[CH2:57][NH2:58]>ClCCl>[C:10]([O:14][C:15](=[O:16])[NH:17][CH2:18][C:19](=[O:21])[NH:58][CH2:57][C:56]([F:60])([F:59])[F:55])([CH3:11])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 2724699PyBOP

Product 1

HCID 71623152HCID 71623152, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (15 ml) is added to a solution of N-(tert-butoxycarbonyl)glycine (5.0 g), PYBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate, 16.3 g) and 2,2,2-trifluoroethylamine (2.47 ml) in dichloromethane (48 ml). After 24 hours at room temperature, the reaction is quenched with water and extracted three times with dichloromethane. The combined organic phases are washed with HOC (2M), Na2CO3 (1M) and a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified by column chromatography (450 g) eluting with a mixture of ethyl acetate and hexane (2:3 to 3:2) to yield [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-carbamic acid tert-butyl ester (3.89 g).

Workup

  1. customthe reaction is quenched with water
  2. extractionextracted three times with dichloromethane
  3. washThe combined organic phases are washed with HOC (2M), Na2CO3 (1M)
  4. dry with materiala saturated aqueous solution of NaCl, dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography (450 g)
  7. washeluting with a mixture of ethyl acetate and hexane (2:3 to 3:2)

Sources & evidence

ORD record
ord-b0214d6800424111bf45dbf725034d91
Source dataset
uspto-grants-2013_02
Patent number
US08383659B2

Reaction notes

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