Tert-butyl 2,2,2-trichloroethanimidate → 3-benzyloxy-2-[N-(tert-butoxycarbonyl)amino]-2-methylpropanoic acid tert-butyl ester

HRID 1669923Notes

Reaction equation

HRID 1669923 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:14])[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](OC(=N)C(Cl)(Cl)Cl)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:12][C:11](=[O:13])[C:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:14])[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 118230233-benzyloxy-2-[N-(tert-butoxycarbonyl)amino]-2-methylpropanoic acid

Product 1

HCID 109813793-benzyloxy-2-[N-(tert-butoxycarbonyl)amino]-2-methylpropanoic acid tert-butyl esterYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the N-Boc carboxylic acid 7 (1.6 g, 5.17 mmol) in 15 mL of CH2Cl2 at room temperature was added a 3 eq portion of tert-butyl-2,2,2-trichloroacetimidate (3.4 g). After overnight stirring at room temperature, the solvent was evaporated under reduced pressure. Purification via silica gel column chromatography (15% EtOAc in hexane) afforded 8 as a colorless oil (1.71 g, 90%): 1H NMR (CDCl3) δ 1.44 (9H, s), 1.45 (9H, s), 1.48 (3H, s), 3.66 (1H, d, J=8.8), 3.79-3.82 (1H, broad d), 4.48-4.58 (2H, m), 5.51 (1H, broad s), 7.28-7.35 (5H, m). Anal. (C20H31NO5) C, H, N.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customPurification via silica gel column chromatography (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-eb7018fa242e46be869d695fc3a216b6
Source dataset
uspto-grants-2011_08
Patent number
US07989649B2

Reaction notes

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