Hydrochloric Acid → HCID 86691115, compound

HRID 928219Notes

Reaction equation

HRID 928219 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([Cl:21])[CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=[N:37][C:32]2[CH:33]=[CH:34]C=[N:36][C:31]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.NC1(C#N)CC1.CCN(C(C)C)C(C)C.Cl>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH:37][C:32]1([C:31]#[N:36])[CH2:34][CH2:33]1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([Cl:21])[CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 21970632N-(tert-Butoxycarbonyl)-3-chloro-L-tyrosine

Product 1

HCID 86691115HCID 86691115, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

(S)-2-(tert-butoxycarbonylamino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid (3.86 g, 12.2 mmol, Eq: 1.00) was dissolved in DMF (50 mL). HATU (9.3 g, 24.4 mmol, Eq: 2.00), 1-amino-1-cyclopropanecarbonitrile hydrochloride (1.74 g, 14.7 mmol, Eq: 1.20) and Hunig's Base (3.16 g, 4.27 mL, 24.4 mmol, Eq: 2.00) were added to the obtained suspension. The reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was poured into aqueous 0.1M HCl (300 mL), extracted with dichloromethane (3×125 mL), dried over Na2SO4, filtered and evaporated. The crude material was purified by flash chromatography (silica gel, 80 g, 0% to 65% AcOEt in n-heptane) to yield a white solid (3.13 g; 67%). m/z=378.1 [M−H]−.

Workup

  1. extractionextracted with dichloromethane (3×125 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by flash chromatography (silica gel, 80 g, 0% to 65% AcOEt in n-heptane)
  6. customto yield a white solid (3.13 g; 67%)

Sources & evidence

ORD record
ord-860ba563972f4e1ea949f1cf1be4add3
Source dataset
uspto-grants-2016_03
Patent number
US09290467B2

Reaction notes

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