1,2-Dichloroethane → 1-tert-Butoxycarbonylamino-cyclobutanecarboxylic acid benzyl ester

HRID 1908651Notes

Reaction equation

HRID 1908651 reaction equation
[C:1]([NH:8][C:9]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)CCl.N1C=CC=CC=1.[CH2:26](O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:26]([O:14][C:13]([C:9]1([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:12][CH2:11][CH2:10]1)=[O:15])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 1049PyridineHCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-

Product 1

HCID 669199311-tert-Butoxycarbonylamino-cyclobutanecarboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2.0 g N-Boc-1-aminocyclobutane carboxylic acid in 100 ml dichloromethane were added 2.1 g EDC, 1.4 g DMAP, 2.2 ml pyridine and 4.8 ml benzyl alcohol. After stirring for 16 h the mixture was diluted with dichloromethane and washed with 0.1 M HCl and saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was purified by chromatography on silica using heptane/ethyl acetate 2/1 as eluent.

Workup

  1. washwashed with 0.1 M HCl and saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-017a97d8b54d4126a4269072619f4656
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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