Triphosgene → HCID 58091390, compound

HRID 2045691Notes

Reaction equation

HRID 2045691 reaction equation
[C:1]([O-])(O)=[O:2].[Na+].Cl.[NH2:7][C@@H:8]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:9]([O:11][CH3:12])=[O:10].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:13]1([C@H:8]([N:7]=[C:1]=[O:2])[C:9]([O:11][CH3:12])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 17747951Methyl (2S)-amino(cyclohexyl)acetate--hydrogen chloride (1/1)

Product 1

HCID 58091390HCID 58091390, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500 mL round-bottom flask was charged with saturated NaHCO3 (80 mL) and DCM (80 ml) and cooled in an ice bath with vigorous stirring. Methyl (2S)-amino(cyclohexyl)acetate hydrochloride (4.0 g, 19.26 mmol) was added followed by triphosgene (1.886 g, 6.36 mmol). The contents of the reaction flask were stirred for 1 hr with cooling, then poured into a reparatory funnel. The layers were separated, and the aqueous layers were extracted with 20 mL DCM. The combined organic portions were dried with anhydrous MgSO4, filtered and evaporated to give the title compound as a colorless oil. 1H NMR (CDCl3): δ 3.90 (d, J 4, 1H), 3.81 (s, 3H), 1.88-1.83 (m, 1H), 1.79-1.76 (m, 2H), 1.69-1.62 (m, 2H), 1.54-1.48 (m, 1H), 1.29-1.11 (m, 5H) ppm.

Workup

  1. temperaturecooled in an ice bath with vigorous stirring
  2. temperaturewith cooling
  3. additionpoured into a reparatory funnel
  4. customThe layers were separated
  5. extractionthe aqueous layers were extracted with 20 mL DCM
  6. dry with materialThe combined organic portions were dried with anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-864feaddfa054d1984467162635da692
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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