Hydrochloric Acid → HCID 66682554, compound

HRID 1175135Notes

Reaction equation

HRID 1175135 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([NH2:17])([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18](N(CC)CC)C.[CH2:25]([O:27][C:28](=[O:33])[CH2:29][C:30](Cl)=[O:31])C.Cl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:18])=[O:14])([NH:17][C:30](=[O:31])[CH2:29][C:28]([O:27][CH3:25])=[O:33])[CH2:11]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 59558354HCID 59558354, compound

Product 1

HCID 66682554HCID 66682554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-3-methoxycarbonylmethyl-azetidine-1-carboxylic acid tert-butyl ester (2 g; 8.2 mmol) dissolved in CH2Cl2 (100 ml) and triethylamine (3.4 ml; 24.5 mmol) is cooled to −5° C. Chlorocarbonyl-acetic acid ethyl ester (1.23 ml; 9.8 mmol) is slowly added under stirring. The reaction mixture is warmed to room temperature, stirred for 20 minutes, poured on 2N HCl (15 ml) and extracted with TBME three times. The organic phases are combined, washed with a saturated solution of NaHCO3, dried over Na2SO4 and evaporated to dryness. Chromatography (SiO2; Hexanes/acetone 7:3) yields the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6): 8.62 (s, 1H); 4.08 (q, 2H); 3.88 (m, 4H); 3.60 (s, 3H); 3.21 (s, 2H); 3.02 (s, 2H); 1.38 (s, 9H); 1.18 (t, 3H). MS (m/z) ES+: 359 (80; MH+); 303 (100);

Workup

  1. stirringstirred for 20 minutes
  2. extractionextracted with TBME three times
  3. washwashed with a saturated solution of NaHCO3
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e8942426768f48858f072f6fa8660a0e
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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