Isopropyl isocyanate → HCID 28737755, compound

HRID 1685372Notes

Reaction equation

HRID 1685372 reaction equation
[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH:13]([N:16]=[C:17]=[O:18])([CH3:15])[CH3:14]>C(Cl)Cl.Cl>[CH:13]([NH:16][C:17]([NH:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5])=[O:18])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 686704(3S)-3-amino-3-phenylpropanoic acid

Product 1

HCID 28737755HCID 28737755, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of (S)-3-amino-3-phenylpropionic acid (1.22 g, 7.3 mmol) and TEA (1.24 mL, 8.86 mmol) in CH2Cl2 (30 mL) at ambient temperature was added isopropyl isocyanate (0.798 mL, 8.12 mmol). The reaction mixture was stirred for 3 h, diluted with 1M HCl (25 mL), and extracted with CH2Cl2 (3×25 mL). The combined CH2Cl2 extracts were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=251 (M+1).

Workup

  1. extractionextracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3da47c77c054fd48560514d0d23504e
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

Loading…