Hydrochloric Acid → HCID 86691114, compound

HRID 928218Notes

Reaction equation

HRID 928218 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([OH:15])=O)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].CN(C(ON1N=[N:39][C:34]2[CH:35]=[CH:36]C=[N:38][C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.NC1(C#N)CC1.Cl.C(OC(C)(C)C)=O>CN(C=O)C>[C:20]([O:19][C:17](=[O:18])[NH:16][C@H:12]([C:13](=[O:15])[NH:39][C:34]1([C:33]#[N:38])[CH2:36][CH2:35]1)[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:10][CH:9]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 61207tert-Butyl FormateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10853202(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]propanoic acidHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochloride

Product 1

HCID 86691114HCID 86691114, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

(S)-3-(4-(allyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoic acid (5 g, 15.6 mmol, Eq: 1.00) was dissolved in DMF (30 ml). HATU (11.8 g, 31.1 mmol, Eq: 2.00), Hunig's Base (4.02 g, 5.43 ml, 31.1 mmol, Eq: 2.00) and 1-amino-1-cyclopropanecarbonitrile hydrochloride (2.21 g, 18.7 mmol, Eq: 1.20) were added to the above suspension and stirred at 25° C. for 24 h. The reaction mixture was poured into 0.1M HCl (250 mL) and extracted with AcOEt (3×75 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was dissolved in CH2Cl2 (10 mL), 2 minutes later it began to precipitate. The suspension was filtered. The filtered solution was purified by flash chromatography (silica gel, 80 g, 0% to 90% AcOEt in heptane) to yield a light yellow solid (3.0 g; 50%). m/z=286.1 [M+H-Boc]+.

Workup

  1. extractionextracted with AcOEt (3×75 mL)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material was dissolved in CH2Cl2 (10 mL), 2 minutes later it
  5. customto precipitate
  6. filtrationThe suspension was filtered
  7. customThe filtered solution was purified by flash chromatography (silica gel, 80 g, 0% to 90% AcOEt in heptane)
  8. customto yield a light yellow solid (3.0 g; 50%)

Sources & evidence

ORD record
ord-3f3094969fbf4bddb69768e4b975708f
Source dataset
uspto-grants-2016_03
Patent number
US09290467B2

Reaction notes

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