1,2-Dichloroethane → HCID 131723084, compound

HRID 897000Notes

Reaction equation

HRID 897000 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].O[N:16]1[C:21](=[O:22])[CH2:20][CH2:19][C:17]1=[O:18].C(Cl)CCl>C1COCC1>[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][C@H:2]1[C:3]([O:5][N:16]1[C:21](=[O:22])[CH2:20][CH2:19][C:17]1=[O:18])=[O:4]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid

Product 1

HCID 131723084HCID 131723084, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Boc-Aze-OH (5 g, 25 mmol) and HOSu (2.88 g, 25 mmol) in 25 ml of THF was cooled on an ice bath EDC (4.3 ml, 25 mmol) was added and the solution was stirred overnight. It was evaporated, dissolved in ethyl acetate, washed with KHSO4 (aq, 0.3 M), Na2CO3 (aq, 10%), dried (MgSO4) and evaporated. Crystallization from ethyl acetate:petroleum ether afforded 3.78 g (51%) of sub-title compound.

Workup

  1. additionwas added
  2. customIt was evaporated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with KHSO4 (aq, 0.3 M), Na2CO3 (aq, 10%)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ccab64015d374164824a8910a3d96ac1
Source dataset
uspto-grants-2005_07
Patent number
US06921758B2

Reaction notes

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