Tert-butyl 2,2,2-trichloroethanimidate → tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-hydroxypropanoate

HRID 1776967

Reaction equation

HRID 1776967 reaction equation
[C:1]([NH:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][OH:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].ClC(Cl)(Cl)C(=N)O[C:29]([CH3:32])([CH3:31])[CH3:30]>CCOC(C)=O.C1CCCCC1>[CH:7]1[C:6]2[CH:5]([CH2:4][O:3][C:1]([NH:18][CH:19]([CH2:20][OH:21])[C:22]([O:24][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:23])=[O:2])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 6541433(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxypropanoic acid

Product 1

HCID 13965220tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-hydroxypropanoateYield 68.3%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of commercial N-Fmoc-L-serine (1.5 g, 4.58 mmol) in EtOAc (40 ml), a solution of t-butyl 2,2,2-trichloroacetimidate (4.00 g, 18.32 mmol) in cyclohexane (18 ml) was added dropwise. After stirring at room temperature for 24 hrs, the solution was evaporated and the residue was purified by flash chromatography (n-Hexane/EtOAc 70:3), yielding the title compound (1.20 g, 68%).

Workup

  1. customthe solution was evaporated
  2. customthe residue was purified by flash chromatography (n-Hexane/EtOAc 70:3)

Sources & evidence

ORD record
ord-28932fd93c5d4c7dbdb19f8ffbd9edea
Source dataset
uspto-grants-2016_02
Patent number
US09266820B2

Linked notes

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