Diisopropylethylamine → HCID 11171741, compound

HRID 1159082Notes

Reaction equation

HRID 1159082 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].C(N(C(C)C)CC)(C)C.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl.C(Cl)Cl.CCOC(C)=O>[O:26]=[C:24]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:4]([C:3]([O:2][CH3:1])=[O:13])[NH:5]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 853474(R)-Methyl 2-amino-3-phenylpropanoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11171741HCID 11171741, compoundYield 60.9%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

D-Phenylalanine methyl ester (1.56 g of HCl salt, Aldrich in CH2Cl2 washed with saturated NaHCO3 and dried, 7.3 mmol) and diisopropylethylamine (2.1 ml, 8.9 mmol) in 1,2-dichloroethane (13 ml) was added dropwise over 30 min to a stirring solution of triphosgene (1.1 g, 5.2 mmol) in 1,2-dichloroethane (13 ml). After stirring at ambient temperature for 1.5 h, the reaction was cooled to 0° C. and aluminum chloride (2.2 g) was added. After refluxing for 2.5 h, the reaction was once again cooled to 0° C. and quenched by slowly adding water (13 ml). After stirring for 1 h, the reaction mixture was transferred to a separatory funnel with CH2Cl2. Extraction with CH2Cl2 (2×) and drying over MgSO4 afforded 1.8 g of crude product. Flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2) afforded pure product (0.65 g, 43% yield). MS (ESI) 206 (M+H).

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. temperatureAfter refluxing for 2.5 h
  3. temperaturethe reaction was once again cooled to 0° C.
  4. customquenched by slowly adding water (13 ml)
  5. stirringAfter stirring for 1 h
  6. customthe reaction mixture was transferred to a separatory funnel with CH2Cl2
  7. extractionExtraction with CH2Cl2 (2×)
  8. dry with materialdrying over MgSO4
  9. customafforded 1.8 g of crude product

Sources & evidence

ORD record
ord-ec2a3c424cee4da4912d028ee380b856
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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