1,2-Dichloroethane → HCID 131723084, compound

HRID 1167075Notes

Reaction equation

HRID 1167075 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. temperaturewas cooled on an ice bath
  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-288bbf67922e4958b0851e0e3b6fa75d
Source dataset
uspto-grants-2003_09
Patent number
US06617320B2

Reaction notes

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